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Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem ‐Dihalocyclopropane Derivatives
Author(s) -
Wang MeiXiang,
Feng GuoQiang,
Zheng QiYu
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303020
Subject(s) - enantiopure drug , nitrile hydratase , chemistry , nitrile , amidase , enantioselective synthesis , amide , biotransformation , substituent , organic chemistry , enantiomer , biocatalysis , hydrolysis , combinatorial chemistry , catalysis , enzyme , reaction mechanism
Catalyzed by Rhodococcus sp. AJ270 microbial cells, trans ‐2,2‐dihalo‐3‐phenylcyclopropanecarbonitriles and ‐amides underwent enantioselective hydrolysis under very mild conditions. Both the efficiency and enantioselectivity of the nitrile hydratase and amidase involved in the cells were strongly determined by the nature of the halogen substituent. The synthetic utility of the biocatalytic process was illustrated by an efficient and multi‐gram scale biotransformation and synthesis of enantiopure 2,2‐dichloro‐3‐phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms.