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

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• 作者：Ryo Shintani ; Yoshitaka Ichikawa ; Tamio Hayashi ; Jinshui Chen ; Yoshiaki Nakao ; Tamejiro Hiyama
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：October 25, 2007
• 年：2007
• 卷：9
• 期：22
• 页码：4643 - 4645
• 全文大小：82K
• 年卷期：v.9,no.22(October 25, 2007)
• ISSN：1523-7052

文摘

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 -silyl ,-unsaturated ketones. By employing (S,S)-Ph-bod* as a ligand, a range of alkenyl nucleophileshave been installed to these substrates in high yield and enantiomeric excess. The resulting allylsilanes can be used for stereoselectiveintramolecular allylation reactions to control two contiguous tertiary and quaternary stereocenters.