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

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.

SUBMITTER: Rainka MP

PROVIDER: S-EPMC395992 | biostudies-literature | 2004 Apr

REPOSITORIES: biostudies-literature

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

Rainka Matthew P MP Aye Yimon Y Buchwald Stephen L SL

Proceedings of the National Academy of Sciences of the United States of America 20040405 16

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 reac ...[more]

PMID: 15067136

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