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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Intramolecular [1,4]-S- to O-silyl migration: a useful strategy for synthesizing Z-silyl enol ethers with diverse
Changzhen Sun1, Yuebao Zhang, Peihong Xiao
1Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, P. R. China.
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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