[1,5]-Anion Relay via Intramolecular Proton Transfer To Generate 3,3-Bis(silyl) Allyloxy Lithium: A Useful Scaffold for Syn-Addition to Aldehydes and Ketones

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• 作者：Xinglong Lin ; Xincui Ye ; Xianwei Sun ; Yuebao Zhang ; Lu Gao ; Zhenlei Song
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：16
• 期：4
• 页码：1084-1087
• 全文大小：355K
• ISSN：1523-7052

文摘

A [1,5]-anion relay has been achieved in 3,3-bis(silyl) benzyl enol ether. Deprotonation at the sterically more accessible benzyl position triggers an intramolecular proton transfer to generate the thermodynamically more stable 3,3-bis(silyl) allyloxy lithium. This endo-oriented allyl anion is stable at 鈭?8 掳C and undergoes diastereoselective syn-addition at the 纬-position with aldehydes and ketones to give monobenzyl-substituted 1,2-diols.