Nucleophilic Displacement at Benzhydryl Centers:  Asymmetric Synthesis of 1,1-Diarylalkyl Derivatives

Activation of substituted 1,1-diarylmethanols as their corresponding toluenesulfonates and subsequent displacement with a range of carbon, nitrogen, oxygen, and sulfur nucleophiles proceeds in 81−96% yield. Enantiomerically enriched diarylmethanols 8a−c were activated and displaced with pyridine ace...

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Bibliographic Details
Published in:Organic letters 2004-01, Vol.6 (1), p.111-114
Main Authors: Bolshan, Yuri, Chen, Cheng-yi, Chilenski, Jennifer R, Gosselin, Francis, Mathre, David J, O'Shea, Paul D, Roy, Amélie, Tillyer, Richard D
Format: Article
Language:English
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Summary:Activation of substituted 1,1-diarylmethanols as their corresponding toluenesulfonates and subsequent displacement with a range of carbon, nitrogen, oxygen, and sulfur nucleophiles proceeds in 81−96% yield. Enantiomerically enriched diarylmethanols 8a−c were activated and displaced with pyridine acetate enolate with complete stereochemical inversion at carbon to yield 1,1-diarylalkyl derivatives 10a−c without loss of optical purity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0361655