Enantioselective Cyanosilylation of ,-Dialkoxy Ketones Catalyzed

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• 作者：Bo Qin ; Xiaohua Liu ; Jian Shi ; Ke Zheng ; Haitao Zhao ; Xiaoming Feng
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：March 30, 2007
• 年：2007
• 卷：72
• 期：7
• 页码：2374 - 2378
• 全文大小：129K
• 年卷期：v.72,no.7(March 30, 2007)
• ISSN：1520-6904

文摘

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Bifunctional N,N'-dioxide catalysts have been developed for highly enantioselective cyanosilylation of,-dialkoxy ketones. This process, catalyzed by in-situ-prepared proline-derived N,N'-dioxide 2b,produced the corresponding cyanohydrin trimethylsilyl ethers in excellent yields (up to 99%) with highenantioselectivities (up to 93% ee). A reasonable mechanism was proposed according to the observationof the linear effect, ¹H NMR spectra, isolated cyanohydrin, and the roles of the NH and N-oxide moietiesof the catalyst.