Sakurai Reaction of 3,3-Bis(silyl) Silyl Enol Ethers with Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid

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• 作者：Linjie Li ; Xincui Ye ; Ya Wu ; Lu Gao ; Zhenlei Song ; Zhiping Yin ; Yongjin Xu
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：March 1, 2013
• 年：2013
• 卷：15
• 期：5
• 页码：1068-1071
• 全文大小：341K
• 年卷期：v.15,no.5(March 1, 2013)
• ISSN：1523-7052

文摘

3,3-Bis(silyl) silyl enol ethers have been shown to exhibit predominantly Sakurai reactivity, rather than Mukaiyama aldol reactivity, in their Lewis acid promoted reactions with acetals. Starting from a geminal bis(silyl) moiety consisting of two different silyl groups, such as SiMe₃ and SiMe₂Ph, the SiMe₃ is selectively eliminated to give monoprotected E- vinylsilyl diols with good to excellent syn-diastereoselectivity. This reaction also underpinned a synthesis of the nematocidal oxylipid from Notheia anomala, demonstrating the attractive bifunctionality of geminal bis(silanes).