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Article

Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams

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Gregory Hughes, Masanari Kimura, and Stephen L. Buchwald*

Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2003, 125 (37), pp 11253–11258

DOI: 10.1021/ja0351692

Publication Date (Web): August 19, 2003

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

, sbuchwal@mit.edu

Abstract

A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of α,β-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl₂·H₂O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (−)-Paroxetine.

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Published In Issue September 17, 2003
Received March 14, 2003

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Article

Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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

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

Synthesis of β-Alkyl Cyclopentanones in High Enantiomeric Excess via Copper-Catalyzed Asymmetric Conjugate Reduction

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