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Asymmetric 1,4-Hydrosilylations of α,β-Unsaturated Esters

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Bruce H. Lipshutz,* Jeff M. Servesko, and Benjamin R. Taft

Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106

J. Am. Chem. Soc., 2004, 126 (27), pp 8352–8353

DOI: 10.1021/ja049135l

Publication Date (Web): June 18, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, lipshutz@chem.ucsb.edu

Abstract

Complexing catalytic amounts of CuH with a nonracemic JOSIPHOS or SEGPHOS ligand, together with stoichiometric PMHS, leads to exceedingly efficient and highly enantioselective 1,4-reductions of β,β-disubstituted enoates and lactones. An unprecedented substrate-to-ligand ratio of 7700:1 for this type of reaction is documented.

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Published In Issue July 14, 2004
Received February 17, 2004

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Communication

Asymmetric 1,4-Hydrosilylations of α,β-Unsaturated Esters

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams

Asymmetric Conjugate Reduction of α,β-Unsaturated Esters Using a Chiral Phosphine−Copper Catalyst

Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds Catalyzed by a Copper Carbene Complex

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