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Enzymes in Organic Synthesis, 18. Lipase‐catalyzed Asymmetric Alcoholysis of 3‐Substituted Pentanedioic Anhydrides
Author(s) -
Ozegowski Rüdiger,
Kunath Annamarie,
Schick Hans
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301126
Subject(s) - chemistry , lipase , organic chemistry , enantiomer , triacylglycerol lipase , enzyme , catalysis , enantiomeric excess , diethyl ether , ether , candida antarctica , enantioselective synthesis
The influence of several enzymes, alcohols, and solvents on the stereochemical outcome of the asymmetric alcoholysis of 3‐substituted pentanedioic anhydrides was investigated. The alcoholysis of 3‐acetoxypentanedioic anhydride ( 5a ) in diethyl ether with 2‐methylpropanol afforded the (3 S )‐monoester ( S )‐ 6a with an enantiomeric excess of > 98% when the lipase from Candida sp. 382 was used as the enzyme. Under the same conditions, 3‐methoxypentanedioic anhydride ( 5c ) was converted by the lipase of Pseudomonas cepacia (Amano PS) into the (3 R )‐monoester ( R )‐ 6c with an e.e. of 90%.