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Title:
PRODUCTION OF OPTICALLY ACTIVE BETA-SUBSTITUTED CARBOXYLIC ACID
Document Type and Number:
Japanese Patent JPS59137441
Kind Code:
A
Abstract:

PURPOSE: Readily available optically active proline is used as an asymmetric source and an organometallic compound is subjected to conjugate addition to its N-α,β-unsaturated carboxylic acid amide derivative in the presence of a tertiary amine and the product is hydrolyzed to effect the high-yield production of the titled substance used as a starting compound for various reagents.

CONSTITUTION: An α,β-unsaturated carboxylic acid amide derivative of optically active proline or hydroxyproline of formula I (R is alkyl, aryl; R1 is H, hydroxyl) is used as an asymmetric source to undergo conjugate addition of at least one selected from organometallic compounds of formula III (X is halogen) and formula II (R" is alkyl, aryl) such as butyl lithium in the presence of a tertiary amine such as trimethylamine in an aprotonic organic solvent under anhydrous conditions, preferably at -40W0°C, then the product is hydrolyzed to give the objective compound.


Inventors:
SOGOU KENZOU
Application Number:
JP1099283A
Publication Date:
August 07, 1984
Filing Date:
January 26, 1983
Export Citation:
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Assignee:
AJINOMOTO KK
International Classes:
C07C53/126; C07B31/00; C07B53/00; C07C51/00; C07C51/06; C07C51/347; C07C57/30; C07C67/00; (IPC1-7): C07C51/347; C07C53/126; C07C57/30