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Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5821-3. Epub 2004 Apr 5.

Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.

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

Abstract

A chiral copper-hydride catalyst for the asymmetric conjugate reduction of alpha,beta-unsaturated carbonyl compounds has been used for the reduction of substrates containing beta-nitrogen substituents. A new set of reaction conditions has allowed for a variety of beta-azaheterocyclic acid derivatives to be synthesized in excellent yields and with high degrees of enantioselectivity. In addition, the effect that the nature of the nitrogen substituent has on the rate of the conjugate reduction reaction has been explored.

PMID:
15067136
PMCID:
PMC395992
DOI:
10.1073/pnas.0307764101
[Indexed for MEDLINE]
Free PMC Article
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