TITLE

Chemoenzymatic synthesis of the chiral herbicide: (S)-metolachlor

AUTHOR(S)
Liangyu Zheng; Suoqin Zhang; Fang Wang; Gui Gao; Shugui Cao
PUB. DATE
August 2006
SOURCE
Canadian Journal of Chemistry;Aug2006, Vol. 84 Issue 8, p1058
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
A chemoenzymatic approach for the production of (S)-metolachlor, one of the most widely used herbicides, has been developed. The starting material (S)-N-(2-ethyl-6-methylphenyl)alanine was obtained by the use of lipase-catalyzed hydrolytic kinetic resolution. Under the optimal conditions, the good activity and excellent enantioselectivity of lipase B from Candida antarctica (CAL-B,E > 100) are achieved in diethyl ether � water (15% v/v), which is about 9.7-fold more enantioselective than that in a pure buffered aqueous solution (E = 12.1). After a simple extraction procedure is used to separate the acid product from the remaining ester, the remaining ester is racemized, providing the basis for the continuous resolution process. Then (S)-metolachlor is synthesized by a simple chemical method using the enantiomerically pure (S)-acid.
ACCESSION #
23061342

 

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