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Chiral copper complex catalyst composition and asymmetric production process using the same

Imported: 23 Feb '17 | Published: 22 Oct '02

Gohfu Suzukamo, Makoto Itagaki, Michio Yamamoto

USPTO - Utility Patents

Abstract

There is disclosed chiral copper complex catalyst composition, which is obtained by contacting an optically active N-salicylideneaminoalcohol compound of formula (1):

with a mono-valent or di-valent copper compound in an inert solvent,

wherein R

1 and R

2 represent an alkyl group and the like,

X

1 and X

2 represent a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group, a cyano group or the like, and

the amount of the mono-valent or di-valent copper compound is less than 1 mole per 1 mole of the optically active N-salicylideneaminoalcohol compound of formula (1), and a process for producing an optically active cylopropane-carboxylic acid ester using the same.

Claims

1. A chiral copper complex catalyst composition,

with a mono-valent or di-valent copper compound in an inert solvent,

2. A process for producing an optically active cyclopropane-carboxylic acid ester of formula (2):

wherein R

3, R

4, R

5 and R

6 are as defined below, and

with a mono-valent or di-valent copper compound, in an inert solvent,

wherein R

3, R

4, R

5 and R

6 independently represent

with a diazoacetic acid ester of formula (4):

N

2CHCO

2R

7  (4)

3. The chiral copper complex catalyst composition according to claim 1, which is obtained by

4. The chiral copper complex catalyst composition according to claim 1 or 3, wherein R

1 represents

5. The chiral copper complex catalyst composition according to claim 4, wherein X

1 represents a chlorine atom, a bromine atom or a nitro group;

6. The composition according to claim 1 or 3, wherein the mono-valent or di-valent copper compound is a copper salt of an organic carboxylic acid having 2 to 15 carbon atoms.

7. The composition according to claim 4, wherein the mono-valent or di-valent copper compound is a copper salt of an organic carboxylic acid having 2 to 15 carbon atoms.

8. The process for producing an optically active cyclopropane-carboxylic acid ester according to claim 2,wherein after contacting the optically active N-salicylideneaminoalcohol compound with the monovalent or di-valent copper compound in an inert solvent, the resulting mixture is contacted with a base, and is optionally washed with water and dehydrated.

9. The process for producing an optically active cyclopropane-carboxylic acid ester according to claim 2 or 8, wherein R

1 represents

10. A process for producing an optically active cyclopropane-carboxylic acid ester as recited in claim 9, wherein