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Highly Enantioselective Carbonyl-ene Reactions Catalyzed by a Hindered Silyl-Salen-Cobalt Complex

Gerri E. Hutson, Apurva H. Dave and Viresh H. Rawal*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email: vrawaluchicago.edu

G. E. Hutson, A. H. Dave, V. H. Rawal, Org. Lett., 2007, 9, 3869-3872.

DOI: 10.1021/ol071342d (free Supporting Information)


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Abstract

Highly enantioselective carbonyl-ene reactions of various 1,1-disubstituted and trisubstituted alkenes with ethyl glyoxylate are catalyzed by a new Co-salen complex under nearly ideal conditions at room temperature using low catalyst loadings. The reaction provides chiral, homoallylic alcohol products in excellent yields, enantioselectivities, and diastereoselectivities.


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Key Words

Ene Reaction, Homoallylic Alcohols


ID: J54-Y2007-3040