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  • Title: Intramolecular [1,4]-S- to O-silyl migration: a useful strategy for synthesizing Z-silyl enol ethers with diverse thioether linkages.
    Author: Sun C, Zhang Y, Xiao P, Li H, Sun X, Song Z.
    Journal: Org Lett; 2014 Feb 07; 16(3):984-7. PubMed ID: 24467633.
    Abstract:
    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.
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