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Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates
Author(s) -
Holt Jarle,
Arends Isabel W. C. E.,
Minnaard Adriaan J.,
Hanefeld Ulf
Publication year - 2007
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.200700053
Subject(s) - cyanohydrin , chemistry , kinetic resolution , candida rugosa , hydrolysis , lipase , organic chemistry , enantiomer , subtilisin , biocatalysis , combinatorial chemistry , enzyme , catalysis , enantioselective synthesis , reaction mechanism
The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of α,α‐disubstituted cyanohydrin acetates, a type of protected tertiary alcohols that form particularly interesting building blocks in organic synthesis. Utilising Subtilisin A the hydrolysis reaction was ( S )‐selective, while Candida rugosa lipase was ( R )‐selective. With these commercially available enzymes both enantiomers of the α,α‐disubstituted cyanohydrin acetates are now accessible.