Copper-Catalyzed Asymmetric Conjugate Reduction as a Route to Novel β-Azaheterocyclic Acid Derivatives

A chiral copper-hydride catalyst for the asymmetric conjugate reduction of α,β-unsaturated carbonyl compounds has been used for the reduction of substrates containing β-nitrogen substituents. A new set of reaction conditions has allowed for a variety of β-azaheterocyclic acid derivatives to be synth...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 2004-04, Vol.101 (16), p.5821-5823
Main Authors: Rainka, Matthew P., Aye, Yimon, Buchwald, Stephen L., Halpern, Jack
Format: Article
Language:English
Subjects:
Acetates
Acids - chemical synthesis
Asymmetric Catalysis Special Feature Part II
Catalysis
Catalysts
Chemistry
Copper
Copper - chemistry
Esters
Flasks
Heterocyclic Compounds - chemical synthesis
Lactams
Nitrogen
Physical Sciences
Reaction kinetics
Room temperature
Solvents
Tetrahedrons
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Summary:A chiral copper-hydride catalyst for the asymmetric conjugate reduction of α,β-unsaturated carbonyl compounds has been used for the reduction of substrates containing β-nitrogen substituents. A new set of reaction conditions has allowed for a variety of β-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.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0307764101