Thiocrown Ether Additive Effects on Diastereoselectivity of the Lipase-Catalyzed Reaction: Preparation of Optically Active 3-Hydroxy-2-methylalkanenitriles through a Double Enzymatic Reaction Strategy

The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselecti...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 72; no. 7; pp. 1589 - 1595
Main Authors Mitsukura, Koichi, Choraku, Hiroko, Da, San Thi, Itoh, Toshiyuki
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.07.1999
Chemical Soc Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
THIACROWN ETHER
SECONDARY ALCOHOLS
ENHANCED REACTION-RATE
ASYMMETRIC-SYNTHESIS
CANDIDA-RUGOSA
ENANTIOSELECTIVITY
PHEROMONE SYNTHESIS
RESOLUTION
HYDROLYSIS
TRANSESTERIFICATION
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Summary:The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.72.1589