Chemocatalytic and biocatalytic approaches to the highly stereoselective reduction of ketones

ORGN 574

David Tellers, david_tellers@merck.com1, Birgit Kosjek, david_tellers@merk.com1, Mirlinda Biba2, and Jeffrey C. Moore2. (1) Department of Process Research, Merck Research Laboratories, PO Box 2000 RY800-C267, Rahway, NJ 07065, (2) Process Research, Merck & Co., Inc, Rahway, NJ 07065
Chiral alcohols are versatile synthetic pre-cursors for building blocks in natural and non-natural compounds. This paper describes our preparation of chiral alcohols via highly enantioselective reduction of prochiral ketones employing both transition metal and enzyme catalysts. In particular, the highly stereoselective (bio)catalytic 1,2-Reduction of an alpha,beta-unsaturated ketone will be described. This paper will focus on both catalyst discovery and the development of conditions suitable for practical implementation of the catalytic processes.