METHOD FOR PRODUCING OPTICALLY ACTIVE VINYLCYCLOPROPANECARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYLCYCLOPROPANEAMINO ACID DERIVATIVE

1 . A method for producing an optically active vinylcyclopropanecarboxylic acid derivative, comprising the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative represented by the general formula (1):

wherein, R is NH 2 , a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, or a substituted or unsubstituted aralkyloxy group having 7 to 11 carbon atoms; M is a hydrogen atom or a metal atom; *1 and *2 indicate asymmetric carbon atoms,

with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound.

2 . The production method according to claim 1 , wherein the optically active amine compound is an optically active 1-arylethylamine derivative represented by the general formula (2):

wherein, R 1 is an alkyl group having 1 to 3 carbon atoms; R 2 is a substituted or unsubstituted aralkyl group having 7 to 11 carbon atoms, or a hydrogen atom; Ar is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; *3 indicates an asymmetric carbon atom.

3 . The production method according to claim 2 , wherein R 1 is a methyl group.

4 . The production, method according to claim 2 , wherein Ar is a phenyl group, a 1-naphthyl group or a 2-naphthyl group.

5 . The production method according to claim 1 , wherein R is NH 2 .

6 . A diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound, represented by the general formula (3):

wherein R is NH 2 , a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, or a substituted or unsubstituted aralkyloxy group having 7 to 11 carbon atoms; M is a hydrogen atom or a metal atom; *1 and *2 indicate asymmetric carbon atoms; R 1 is an alkyl group having 1 to 3 carbon atoms; R 2 is a substituted or unsubstituted aralkyl group having 7 to 11 carbon atoms, or a hydrogen atom; Ar is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; *3 indicates an asymmetric carbon atom.

7 . The salt according to claim 6 , wherein R 1 is a methyl group.

8 . The salt according to claim 6 , wherein Ar is a phenyl group, a 1-naphthyl group or a 2-naphthyl group.

9 . The salt according to claim 6 , wherein R is NH 2 .

10 . A method for producing a vinylcyclopropaneamino acid represented by the general formula (6):

wherein *6 and *7 indicate asymmetric carbon atoms,

comprising the step of reacting a vinylcyclopropaneamidecarboxylic acid derivative represented by the general formula (5):

wherein R 5 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 11 carbon atoms, or a metal atom; *4 and *5 indicate asymmetric carbon atoms,

or the salt thereof with a halogenating agent in the presence of a base.

11 . A method for producing a vinylcyclopropaneamino acid derivative represented by the general formula (4):

wherein R 4 is a substituted or unsubstituted alkyloxycarbonyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aralkyloxycarbonyl group having 7 to 12 carbon atoms, a substituted or unsubstituted acyl group having 2 to 12 carbon atoms, or a hydrogen atom; *6 and *7 are the same as the above,

comprising the step of protecting the amino group of the vinylcyclopropaneamino acid produced by the method according to claim 10 .

12 . The production method according to claim 10 , wherein the vinylcyclopropaneamidecarboxylic acid derivative is the optically active vinylcyclopropaneamidecarboxylic acid derivative or the diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound produced by the method comprising the step of reacting reacting a racemic vinylcyclopropanecarboxylic acid derivative represented by the general formula (1):

wherein, R is NH 2 , a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, or a substituted or unsubstituted aralkyloxy group having 7 to 11 carbon atoms; M is a hydrogen atom or a metal atom; *1 and *2 indicate asymmetric carbon atoms,

with an optically active amine compound.

13 . The production method according to claim 11 , wherein the vinylcyclopropaneamidecarboxylic acid derivative is the optically active vinylcyclopropaneamidecarboxylic acid derivative or the diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound produced by the method comprising the step of reacting reacting a racemic vinylcyclopropanecarboxylic acid derivative represented by the general formula (1):

wherein, R is NH 2 , a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, or a substituted or unsubstituted aralkyloxy group having 7 to 11 carbon atoms; M is a hydrogen atom or a metal atom; *1 and *2 indicate asymmetric carbon atoms,

with an optically active amine compound.

14 . The production method according to claim 3 , wherein Ar is a phenyl group, a 1-naphthyl group or a 2-naphthyl group.

15 . The production method according to claim 2 , wherein R is NH 2 .

16 . The production method according to claim 3 , wherein R is NH 2 .

17 . The production method according to claim 4 , wherein R is NH 2 .

18 . The salt according to claim 7 , wherein Ar is a phenyl group, a 1-naphthyl group or a 2-naphthyl group.

19 . The salt according to claim 7 , wherein R is NH 2 .

20 . The salt according to claim 8 , wherein R is NH 2 .