Ahmad, K. and Koul, S. and Taneja, S.C. and Singh, A.P. and Kapoor, M. and Riyaz, Hassan and Verma, V. and Qazi, G.N. (2004) Enzyme directed diastereoselectivity in chemical reductions: studies towards the preparation of all four isomers of 1-phenyl-1,3-butanediol. Tetrahedron: Asymmetry, 15 (11). pp. 1685-1692. ISSN 09574166

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Abstract

Enzymes play an important role in guiding the diastereoselectivity of the final products during the chemical reduction of the intermediates (R)- and (S)-3-hydroxy-1-phenyl-1-butanone, prepared by bioreduction of 1-phenyl-1,3-butadione. For example,the presence of an oxidoreductase such as Pichia capsulata during a one pot, two step, enzymo-chemical reduction of 1-phenyl-1,3- butadione produced corresponding (1R,3S)-1-phenyl-1,3-butanediol (de�98%), similarly Zygosaccharomyces rouxii furnished(1S,3R)-1-phenyl-1,3-butanediol (de�98%). On the other hand chemical reduction of (R)- and (S)-3-hydroxy-1-phenyl-1-butanone after the exclusion of the enzymes resulted in complete loss of diastereoselectivity, leading to the formation of all four isomers of 1-phenyl-1,3-butanediol. Moreover the yields of the final products are higher in the one-pot transformations than in the two step sequential reactions.

Item Type:	Article
Subjects:	Biological Sciences Chemical Sciences
Divisions:	UNSPECIFIED
Depositing User:	Mr. Amit Nargotra
Date Deposited:	03 Jan 2012 05:34
Last Modified:	03 Jan 2012 05:34
URI:	http://iiim.csircentral.net/id/eprint/371

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