Chiral synthesis of secondary alcohols using Geotrichum candidum

Chiral synthesis of secondary alcohols of both the (S)‐ and (R)‐enantiomer with extremely high enantioselectivities (up to >99% ee) using a biocatalyst, Geotrichum candidum, is reviewed. Resting cell and dried‐cell preparation using acetone were applied to oxidation, reduction, and deracemization...

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Published inChirality (New York, N.Y.) Vol. 14; no. 9; pp. 703 - 708
Main Authors Nakamura, Kaoru, Matsuda, Tomoko, Harada, Tadao
Format Journal Article
LanguageEnglish
Published New York Wiley Subscription Services, Inc., A Wiley Company 2002
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Summary:Chiral synthesis of secondary alcohols of both the (S)‐ and (R)‐enantiomer with extremely high enantioselectivities (up to >99% ee) using a biocatalyst, Geotrichum candidum, is reviewed. Resting cell and dried‐cell preparation using acetone were applied to oxidation, reduction, and deracemization reactions. Many methods to improve the reactivity and enantioselectivity of the reactions were developed. For example, additives such as secondary alcohols and hydrophobic resin (Amberlite™ XAD) were used in nonaqueous reaction media such as organic and supercritical solvents as well as in aqueous ones. As a result, optically pure alcohols of both enantiomers were synthesized on a gram scale. Chirality 14:703–708, 2002. © 2002 Wiley‐Liss, Inc.
Bibliography:Nagase Science and Technology Foundation
ark:/67375/WNG-1PF1QVB2-Q
Ministry of Education, Science, Sports and Culture of Japan - No. 12740400; No. 11640602
Taisho Pharmaceutical Co. Award in Synthetic Organic Chemistry, Japan
Sasakawa Scientific Research Grant from the Japan Science Society
ArticleID:CHIR10129
istex:35FA36BD4FBEE31256C2C4370C107C96E61ABE76
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.10129