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Enantioselective Synthesis of Protected Cyanohydrins
Author(s) -
Veum Lars,
Kuster Marina,
Telalovic Selvedin,
Hanefeld Ulf,
Maschmeyer Thomas
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:9<1516::aid-ejoc1516>3.0.co;2-c
Subject(s) - enantioselective synthesis , chemistry , cyanohydrin , combinatorial chemistry , organic chemistry , catalysis
A straightforward process for the preparation of optically active protected cyanohydrins, important building blocks for the synthesis of drugs and agrochemicals, has been established. Lipase B from Candida Antarctica (CAL‐B) catalysed the kinetic resolution of racemic cyanohydrin acetates under mild conditions. The resulting labile cyanohydrins were reprotected either by an enzyme‐catalysed route involving the addition of vinyl butyrate, or chemically after removal of the enzyme from the reaction mixture. This process gave access to both enantiomers in pure form and in good yields, while considerably reducing the risks due to HCN. A variety of different protection groups have also been introduced. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)