Enantioselective, Cyclopentene-Forming Annulations via NHC-Catalyzed Benzoin−Oxy-Cope Reactions

Chiral N-heterocyclic carbene catalysts generated from triazolium salts promote the cyclopentene-forming annulation of α,β-unsaturated aldehydes and 4-oxoenoates with excellent levels of enantioinduction and preference for the cis-1,3,4-trisubstituted cyclopentene diastereomer. Although the observed...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-03, Vol.129 (12), p.3520-3521
Main Authors: Chiang, Pei-Chen, Kaeobamrung, Juthanat, Bode, Jeffrey W
Format: Article
Language:English
Subjects:
Benzoin - chemistry
Catalysis
Cyclopentanes - chemistry
Heterocyclic Compounds - chemistry
Hydrocarbons - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Oxygen - chemistry
Stereoisomerism
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Summary:Chiral N-heterocyclic carbene catalysts generated from triazolium salts promote the cyclopentene-forming annulation of α,β-unsaturated aldehydes and 4-oxoenoates with excellent levels of enantioinduction and preference for the cis-1,3,4-trisubstituted cyclopentene diastereomer. Although the observed products could arise by conjugate additions of catalytically generated homoenolates, our mechanistic and stereochemical investigations strongly support a novel reaction manifold featuring an intermolecular crossed-benzoin reaction and an NHC-catalyzed oxy-Cope rearrangement.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0705543