Thiocrown Ether Additive Effects on Diastereoselectivity of the Lipase-Catalyzed Reaction

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; p. 1589
Main Authors Mitsukura, Koichi, Choraku, Hiroko, Thi Da, San, Itoh, Toshiyuki
Format Journal Article
LanguageEnglish
Published Tokyo Chemical Society of Japan 01.07.1999
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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