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J Am Chem Soc. 2003 Sep 17;125(37):11253-8.

Catalytic enantioselective conjugate reduction of lactones and lactams.

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1
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Abstract

A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-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 CuCl(2).H(2)O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.

PMID:
16220945
DOI:
10.1021/ja0351692
[Indexed for MEDLINE]
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