Intramolecular [1,4]-S- to O-Silyl Migration: A Useful Strategy for Synthesizing Z-Silyl Enol Ethers with Diverse Thioether Linkages

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• 作者：Changzhen Sun ; Yuebao Zhang ; Peihong Xiao ; Hongze Li ; Xianwei Sun ; Zhenlei Song
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：16
• 期：3
• 页码：984-987
• 全文大小：389K
• ISSN：1523-7052

文摘

An intramolecular [1,4]-S- to O-silyl migration has been used to form silyl enol ethers with Z-configurational control. The silyl migration also creates a new anion center at sulfur, which can subsequently react with electrophiles to generate Z-silyl enol ethers with diverse thioether linkages. The synthetic utility of this pathway was demonstrated by modifying the Z-silyl enol ethers with aldehydes via a Mukaiyama aldol reaction or Prins cyclization to generate functionalized organosulfur compounds.