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Chiral synthesis of secondary alcohols using Geotrichum candidum
Author(s) -
Nakamura Kaoru,
Matsuda Tomoko,
Harada Tadao
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10129
Subject(s) - chemistry , geotrichum , amberlite , enantiomer , organic chemistry , acetone , biocatalysis , chirality (physics) , enantioselective synthesis , enantiomeric excess , reactivity (psychology) , aqueous solution , aldol reaction , catalysis , ionic liquid , adsorption , chiral symmetry breaking , physics , quantum mechanics , pathology , nambu–jona lasinio model , quark , medicine , food science , alternative medicine
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.