Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 12, Pages 3520-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0705543
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Chiral N-heterocyclic carbene catalysts generated from triazolium salts promote the cyclopentene-forming annulation of alpha,beta-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.
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