Catalytic enantioselective conjugate reduction of lactones and lactams

G Hughes, M Kimura, SL Buchwald

Index: Hughes, Gregory; Kimura, Masanari; Buchwald, Stephen L. Journal of the American Chemical Society, 2003 , vol. 125, # 37 p. 11253 - 11258

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Citation Number: 206

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.

~51%

~81%

~82%

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