The scope and limitation of the [1,4]-SPh shift in the synthesis of allylic alcohols

VK Aggarwal, J Eames*, Maria A. de las Heras, Sara McIntyre, Stuart Warren

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

Treatment of a series of 4-phenylsulfanyl-1,3-diols with toluene-p-sulfonyl chloride in pyridine gives stereospecifically substituted allylic alcohols in near quantitative yield via a [1,4]-SPh shift. We comment on the structural variation at both the migration origin and terminus on the outcome of the title reaction and define its limits.

Translated title of the contributionThe scope and limitation of the [1,4]-SPh shift in the synthesis of allylic alcohols
Original languageEnglish
Pages (from-to)4456-4461
Number of pages6
JournalPerkin 1
Volume2000
Issue number24
DOIs
Publication statusPublished - 2000

Keywords

  • P-SULFONYL CHLORIDE
  • SUBSTITUTED 1,N-DIOLS
  • PHENYLTHIO MIGRATION
  • TETRAHYDRO-FURANS
  • PYRANS
  • ACID

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