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Synfacts 2009(1): 0061-0061  
DOI: 10.1055/s-0028-1087405
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Chlorohydrin Acetates by Combined Enzyme and Metal Catalysis

Contributor(s): Mark Lautens, Frédéric Ménard
A. Träff, K. Bogár, M. Warner, J.-E. Bäckvall*
Stockholm University, Sweden
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

A highly efficient preparation of enantiopure chlorohydrin acetates is reported. The method combines two known, but very different catalytic processes. On the one hand, enzymes convert ‘matched’ epimers of the alcohols 1 into acetates. Concomitantly, a ruthenium(II) catalyst racemizes the ‘unmatched’ alcohols. Therefore, the combination of the reactions permits a 100% theoretical yield of desired chiral product instead of the 50% maximum yield expected for a classic kinetic resolution.