1-8. (canceled)
9. A method for stereoselectively producing a compound represented by the following formula (I):
comprising:
initiating a reaction of a compound represented by the formula (II):
with a compound represented by the formula (III):
R18\u2014W\u2003\u2003(III)
in a medium in the presence of an optically-active phase-transfer catalyst and an aqueous inorganic base solution; and
quenching the reaction at a time earlier than a time for completion of a stoichiometric reaction of the compound represented by the formula (II) with the compound represented by the formula (III);
wherein in the formula (I) and the formula (II),
R15 is an aryl group or a heteroaryl group that may be substituted with at least one group selected from the group consisting of:
a C1 to C8 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C8 alkyl group that may be branched and that may be substituted with a halogen atom, or a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
R20 is \u2014OR19 (where R19 is a C1 to C8 alkyl group that may be substituted with a halogen atom or an aryl group that may be substituted with a halogen atom, and that may be branched or form a cyclic group) or \u2014NR50R51 (where R50 and R51 are each independently a hydrogen atom, \u2014CHR28R29 (where R28 is a group selected from the group consisting of a hydrogen atom, and an aryl group that may be substituted with a C1 to C4 alkyl group that may be substituted with a halogen atom, a C1 to C3 alkoxy group that may be substituted with a halogen atom, or a halogen atom, and R29 is an aryl group that may be substituted with a C1 to C4 alkyl group that may be substituted with a halogen atom, a C1 to C3 alkoxy group that may be substituted with a halogen atom, or a halogen atom) or \u2014OR101 (where R101 is a C1 to C8 alkyl group or a benzyl group));
wherein in the formula (I) and the formula (III),
R18 is a group selected from the group consisting of:
(i) a C1 to C10 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom, wherein the alkyl group may be substituted with at least one group selected from the group consisting of:
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a halogen atom,
\u2014COR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
\u2014CO2R9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom);
(ii) a C3 to C15 alkyl group or substituted allyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iii) a C2 to C6 alkenyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iv) a C2 to C6 alkynyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(v) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
the alkyl moiety of the aralkyl group is a C1 to C6 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(vi) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
the alkyl moiety of the heteroaralkyl group is a C1 to C6 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom; and
(vii) a C3 to C9 propargyl group or substituted propargyl group that may be branched and that may be substituted with a halogen atom;
wherein in the formula (III),
W is a functional group that has a leaving ability;
wherein in the formula (I) and the formula (II),
n is an integer from 1 to 4; and
wherein in the formula (I),
* shows a newly produced asymmetric center.
10. The method of claim 9, wherein the optically-active phase-transfer catalyst is an optically-active quaternary ammonium salt phase-transfer catalyst or a phase-transfer catalyst complexed with an optically-active metal atom.
11. The method of claim 10, wherein the optically-active quaternary ammonium salt phase-transfer catalyst is an optically-active quaternary ammonium salt that has a biphenyl backbone andor binaphthyl backbone, or an optically-active cinchona alkaloid quaternary ammonium salt.
12. The method of claim 10, wherein the optically-active quaternary ammonium salt phase-transfer catalyst is an optically-active quaternary ammonium salt, or an enantiomer thereof, which is represented by:
(where R\u2033 is a hydrogen atom, a C1 to C4 alkyl group that may be branched, a C1 to C5 alkoxy group that may be branched, or a halogen atom),
(where R is a hydrogen atom or an allyl group, and Z is Cl or Br),
(where R is a methyl group or a hydrogen atom),
13. The method of claim 11, wherein the optically-active quaternary ammonium salt phase-transfer catalyst that has a biphenyl backbone andor binaphthyl backbone is an optically-active quaternary ammonium salt represented by:
wherein
R21 and R22 are each independently a group selected from the group consisting of:
(i) a hydrogen atom;
(ii) \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom);
(iii) a cyano group;
(iv) a nitro group;
(v) a carbamoyl group;
(vi) an N\u2014(C1 to C4 alkyl)carbamoyl group;
(vii) an N,N-di(C1 to C4 alkyl)carbamoyl group;
(viii) \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom);
(ix) a halogen atom;
(x) a C1 to C6 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(xi) a C2 to C6 alkenyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(xii) a C2 to C6 alkynyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(xiii) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(xiv) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(xv) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
or may be substituted with \u2014O\u2014(CH2)p\u2014O\u2014 (where p is 1 or 2) at positions 3 and 4 that are taken together; and
(xvi) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(xvii) \u2014S(O)n\u2014R (where n is 0, 1, or 2, and R is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom);
R25, R25\u2032, R26, and R26\u2032 are each independently a group selected from the group consisting of:
(i) a hydrogen atom;
(ii) a halogen atom;
(iii) an alkyl group, wherein the alkyl group is a C1 to C5 alkyl group that may be substituted with a halogen atom andor an aryl group, andor that may be branched or form a cyclic group; and
(iv) an alkoxy group, wherein the alkoxy group is a C1 to C5 alkoxy group that may be substituted with a halogen atom andor an aryl group, andor that may be branched or form a cyclic group;
R27 and R27\u2032 are each independently a group selected from the group consisting of:
(i) a halogen atom;
(ii) an alkyl group, wherein the alkyl group is a C1 to C5 alkyl group that may be substituted with a halogen atom andor an aryl group, andor that may be branched or form a cyclic group; and
(iii) an alkoxy group, wherein the alkoxy group is a C1 to C5 alkoxy group that may be substituted with a halogen atom andor an aryl group, andor that may be branched or form a cyclic group;
R23 and R24 are each independently a group selected from the group consisting of:
(i) a C1 to C30 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(ii) a C2 to C12 alkenyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iii) a C2 to C12 alkynyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iv) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(v) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(vi) \u2014(CH2)nOCONR10R11 (where R10 and R11 are each independently a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) a C2 to C6 alkenyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(4) a C2 to C6 alkynyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(5) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(6) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
(7) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(8) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(vii) \u2014(CH2)nCONR12R13 (where R12 and R13 are each independently a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(viii) \u2014(CH2)nNR12COR13 (where R12 and R13 are each independently a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(ix) \u2014(CH2)nNR12R13 (where R12 and R13 are each independently a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(x) \u2014(CH2)nY\u2014OR12 (where Y is a C1 to C4 divalent saturated hydrocarbon group that may be branched, and R12 is a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(xi) \u2014(CH2)n\u2014OR12 (where R12 is a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(xii) \u2014(CH2)n\u2014S\u2014R12 (where R12 is a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12);
(xiii) \u2014(CH2)n\u2014SO\u2014R12 (where R12 is a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR10R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR13R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12); and
(xiv) \u2014(CH2)n\u2014SO2\u2014R12 (where R12 is a group selected from the group consisting of:
(1) a hydrogen atom;
(2) a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom;
(3) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
(4) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30) and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
and n is an integer from 1 to 12); or
R23 and R24 are taken together to form a divalent group selected from the group consisting of:
\u2014(CH2)m\u2014 (where m is an integer from 2 to 8);
and
X\u2212 is a halide anion.
14. The method of claim 10, wherein the phase-transfer catalyst complexed with an optically-active metal atom is a metal complex, or an enantiomer thereof, which is represented by:
(where M is Ni or Cu).
15. The method of claim 9, wherein at the time earlier than a time for completion of the stoichiometric reaction, an optical purity of the compound represented by the formula (I) is 70% ee or more.
16. A method for stereoselectively producing a compound represented by the following formula (I):
comprising:
initiating a reaction of a compound represented by the formula (II):
with a compound represented by the formula (III):
R18\u2014W\u2003\u2003(III)
in a medium in the presence of an optically-active phase-transfer catalyst and an aqueous inorganic base solution; and
quenching the reaction at a time t that satisfies the following inequality:
50
<
A
t
\ue8a0
(
%
\ue89e
\ue89e
ee
)
\xd7
YLD
t
\ue8a0
(
%
)
100
<
100
(where
At is the optical purity (% ee) of the compound represented by the formula (I) that is obtained by quenching the reaction at a time t from the initiation of the reaction; and
YLDt is the yield (%) of the compound represented by the formula (I) that is obtained by quenching the reaction at a time t from the initiation of the reaction);
wherein in the formula (I) and the formula (II),
R15 is an aryl group or a heteroaryl group that may be substituted with at least one group selected from the group consisting of:
a C1 to C8 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C8 alkyl group that may be branched and that may be substituted with a halogen atom, or a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom;
R20 is \u2014OR19 (where R19 is a C1 to C8 alkyl group that may be substituted with a halogen atom or an aryl group that may be substituted with a halogen atom, and that may be branched or form a cyclic group) or \u2014NR50R51 (where R50 and R51 are each independently a hydrogen atom, \u2014CHR28R29 (where R28 is a group selected from the group consisting of a hydrogen atom, and an aryl group that may be substituted with a C1 to C4 alkyl group that may be substituted with a halogen atom, a C1 to C3 alkoxy group that may be substituted with a halogen atom, or a halogen atom, and R29 is an aryl group that may be substituted with a C1 to C4 alkyl group that may be substituted with a halogen atom, a C1 to C3 alkoxy group that may be substituted with a halogen atom, or a halogen atom) or \u2014OR101 (where R101 is a C1 to C8 alkyl group or a benzyl group));
in the formula (I) and the formula (III),
R18 is a group selected from the group consisting of:
(i) a C1 to C10 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom, wherein the alkyl group may be substituted with at least one group selected from the group consisting of
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a halogen atom,
\u2014COR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
\u2014CO2R9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom);
(ii) a C3 to C15 alkyl group or substituted allyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iii) a C2 to C6 alkenyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(iv) a C2 to C6 alkynyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(v) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
the alkyl moiety of the aralkyl group is a C1 to C6 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom;
(vi) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of:
a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom,
a C1 to C5 alkoxy group that may be branched and that may be substituted with a halogen atom,
an aryl group that may be substituted with a halogen atom, a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom, a cyano group, \u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), a nitro group, a carbamoyl group, an N\u2014(C1 to C4 alkyl)carbamoyl group, an N,N-di(C1 to C4 alkyl)carbamoyl group, or \u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a cyano group,
\u2014NR30R31 (where R30 and R31 are each independently a hydrogen atom or a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom),
a nitro group,
a carbamoyl group,
an N\u2014(C1 to C4 alkyl)carbamoyl group,
an N,N-di(C1 to C4 alkyl)carbamoyl group,
\u2014NHCOR9 (where R9 is a C1 to C4 alkyl group that may be branched and that may be substituted with a halogen atom), and
a halogen atom; and
the alkyl moiety of the heteroaralkyl group is a C1 to C6 alkyl group that may be branched or form a cyclic group and that may be substituted with a halogen atom; and
(vii) a C3 to C9 propargyl group or substituted propargyl group that may be branched and that may be substituted with a halogen atom;
in the formula (III),
W is a functional group that has a leaving ability;
in the formula (I) and the formula (II),
n is an integer from 1 to 4; and
in the formula (I),
* shows a newly produced asymmetric center.
17. The method of claim 9, wherein the medium is selected from the group consisting of benzene, toluene, xylene, ethyl ether, isopropyl ether, tetrahydrofuran, dioxane, methyl tert-butyl ether, and cyclopentyl methyl ether.
18. The method of claim 9, wherein the medium is a biphasic medium containing water and a water-immiscible medium, the water-immiscible medium is selected from the group consisting of benzene, toluene, xylene, ethyl ether, isopropyl ether, methyl tert-butyl ether, and cyclopentyl methyl ether.
19. The method of claim 16, wherein the medium is selected from the group consisting of benzene, toluene, xylene, ethyl ether, isopropyl ether, tetrahydrofuran, dioxane, methyl tert-butyl ether, and cyclopentyl methyl ether.
20. The method of claim 16, wherein the medium is a biphasic medium containing water and a water-immiscible medium, the water-immiscible medium is selected from the group consisting of benzene, toluene, xylene, ethyl ether, isopropyl ether, methyl tert-butyl ether, and cyclopentyl methyl ether.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A system for producing a rotor-blade spar cap with pultruded rods made of a fiber-reinforced material, the system comprising:
at least one retaining apparatus for rotatably mounting at least one rod-layer roll with a rolled-up layer of pultruded rods arranged one beside the other;
a laminating mold for receiving layers of pultruded rods;
at least one guiding apparatus; and
at least one trimming apparatus for trimming the layers of pultruded rods;
wherein the guiding apparatus is configured to guide onto the laminating mold a layer of pultruded rods which has been unrolled from a rod-layer roll rotatably mounted on the at least one retaining apparatus, and
wherein the at least one trimming apparatus is a sawing apparatus andor a milling apparatus.
2. The system as claimed in claim 1, wherein the retaining apparatus has a drive apparatus andor a braking apparatus for the rod-layer roll rotatably mounted in the retaining apparatus andor at least one force-activated pressure-exerting roller, which presses onto the rolled-up rod layer.
3. The system as claimed in claim 2, wherein at least one sensor is arranged in the guiding apparatus andor on the pressure-exerting roller andor on an arrangement which subjects the pressure-exerting roller to force-activation, wherein there is a signal-transmission channel from the at least one sensor to a control or regulating apparatus of the drive apparatus andor braking apparatus, and the control or regulating apparatus is configured to control or to regulate movement of the rod-layer roll in dependence on transmitted sensor signals.
4. The system as claimed in claim 1, wherein the system further comprises a control apparatus for the at least one guiding apparatus, which is configured to track the position of the at least one guiding apparatus in respect of its vertical andor horizontal position in relation to the laminating mold in dependence on a position of a surface of an uppermost layer of pultruded rods in the laminating mold.
5. The system as claimed in claim 1, wherein the at least one guiding apparatus has guiding rollers, between which runs the layer of pultruded rods, and wherein there is at least one contactless sensor andor at least one running-wheel sensor for measuring a paid-out length of a layer of pultruded rods.
6. The system as claimed in claim 5, wherein at least one of said guiding rollers has a drive andor a brake.
7. The system as claimed in claim 1, wherein the sawing apparatus andor the milling apparatus areis designed to generate a scarf joint in a thickness direction andor to execute a severing action at an angle to a longitudinal axis of the layer of the pultruded rods.
8. The system as claimed in claim 1, wherein the trimming apparatus has a dust-tight enclosure and a connection for a dust-extraction apparatus.
9. The system as claimed in claim 1, wherein the retaining apparatus, the guiding apparatus andor the trimming apparatus areis installed in a stationary manner or on a supporting apparatus which can be moved essentially parallel to a surface of the laminating mold.
10. The system as claimed in claim 1, wherein, in order to set down alternating sequences of layers with offset rods in individual layers, there are two retaining apparatuses provided for two rod-layer rolls, wherein the two retaining apparatuses are arranged both at a same end of the laminating mold or at opposite ends of the laminating mold or on a movable supporting apparatus.
11. The system as claimed in claim 10, wherein, in order to produce the rotor-blade spar cap, two rod-layer rolls each with a peripheral rod of smaller width than remaining rods of the layer are arranged in the two retaining apparatuses such that peripheral rods of smaller width are arranged on different sides, as viewed in relation to the laminating mold.
12. A method for producing a rotor-blade spar cap with pultruded rods made of a fiber-reinforced material, wherein a sequence of layers with pultruded rods made of a fiber-reinforced material arranged one beside each other is set down one above the other in a laminating mold using a system as claimed in claim 1, comprising:
unrolling the layers in alternating fashion from two rod-layer rolls each having, along one periphery, a rod of smaller width than a rest of the rods of the layer; and
arranging the peripheral rods of smaller width different sides, as viewed in relation to the laminating mold.
13. The method as claimed in claim 12, wherein the rod-layer rolls are displaced over the laminating mold together on a movable supporting apparatus, and wherein, in the case of a movement in one direction, a layer is unrolled from one rod-layer roll and, in the case of a movement in the opposite direction, a layer is unrolled from the other rod-layer roll.
14. The method as claimed in claim 12, wherein the layers are unrolled from retaining apparatuses which are installed in a stationary manner at one end, or at opposite ends, of the laminating mold.
15. The method as claimed in claim 12, wherein an operation of rolling out material between the rod-layer roll and guiding apparatus takes place in a force-free manner.
16. The system as claimed in claim 2, wherein the at least one pressure-exerting roller has a soft surface.
17. The system as claimed in claim 7, wherein the scarf joint is at a scarf-joint angle between 2\xb0 and 10\xb0 to a surface of the layer andor at an angle of 90\xb0 to \xb145\xb0 to the longitudinal axis of the layer.