Catalytic Asymmetric Synthesis of Allylsilanes through Rhodium/Chiral Diene-Catalyzed 1,4-Addition of Alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes

A new synthetic method of chiral allylsilanes has been developed through a rhodium-catalyzed asymmetric 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes to β-silyl α,β-unsaturated ketones. By employing (S,S)-Ph-bod* as a ligand, a range of alkenyl nucleophiles have been installed to t...

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Bibliographic Details
Published in:Organic letters 2007-10, Vol.9 (22), p.4643-4645
Main Authors: Shintani, Ryo, Ichikawa, Yoshitaka, Hayashi, Tamio, Chen, Jinshui, Nakao, Yoshiaki, Hiyama, Tamejiro
Format: Article
Language:English
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Summary:A new synthetic method of chiral allylsilanes has been developed through a rhodium-catalyzed asymmetric 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes to β-silyl α,β-unsaturated ketones. By employing (S,S)-Ph-bod* as a ligand, a range of alkenyl nucleophiles have been installed to these substrates in high yield and enantiomeric excess. The resulting allylsilanes can be used for stereoselective intramolecular allylation reactions to control two contiguous tertiary and quaternary stereocenters.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702125q