Highly Efficient Route for Enantioselective Preparation of Chlorohydrins via Dynamic Kinetic Resolution

Annika Träff, Krisztián Bogár, Madeleine Warner and Jan-E. Bäckvall

*Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden, Email: jeborgan.su.se

A. Träff, K. Bogár, M. Warner, J.-E. Bäckvall, Org. Lett., 2008, 10, 4807-4810.

DOI: 10.1021/ol801749z

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Abstract

Dynamic kinetic resolution (DKR) of various aromatic chlorohydrins using Pseudomonas cepacia lipase (PS-C “Amano” II) and a ruthenium catalyst afforded chlorohydrin acetates in high yields and high enantiomeric excesses. These optically pure chlorohydrin acetates can be transformed to a wide range of important chiral compounds.

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Highly Compatible Metal and Enzyme Catalysts for Efficient Dynamic Kinetic Resolution of Alcohols at Ambient Temperature

B. Martin-Matute, M. Edin, Krisztian Bogar, J.-E. Baeckvall, Angew. Chem. Int. Ed., 2004, 43, 6535-6539.

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Key Words

Enantioselective Esterification, Epoxides

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ID: J54-Y2008-3170