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Enzymatic Syntheses of Chiral Building Blocks from Racemates: Preparation of (1 R ,3 R )‐Chrysanthemic, ‐Permethrinic and ‐Caronic Acids from Racemic, Diastereomeric Mixtures
Author(s) -
Schneider Manfred,
Engel Norbert,
Boensmann Heike
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198400641
Subject(s) - diastereomer , chemistry , hydrolysis , enantioselective synthesis , organic chemistry , esterase , enzymatic hydrolysis , enzyme , stereochemistry , catalysis
The use of enantioselectivley reactive enzymes on the laboratory scale offers great advantages. With procine liver esterase, for example, chrysanthemic acid (1 R ,3 R )‐ 1 can be prepared from a mixture of the four esters with (1 S ,3 R )‐, (1 R ,3 S )‐ (1 S ,3 S )‐, and (1 R ,3 R )‐configuration. Diastereoselective hydrolysis of the mixture affords the trans ‐acids (1 S ,3 S )‐1 and (1 R ,3 R )‐1. Enantioselective hydrolysis of the trans ‐ester leads to (1 R ,3 R )‐1, which is of interest in connection with the pyrethroid insecticides.