Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Steven A. Weissman, Kai Rossen, Paul J. Reider

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

(Equation presented) The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols (4), readily accessed from the styrene derivative (5), has been demonstrated to provide the corresponding styrene oxides (2) with high levels of stereoretention (up to 99%) Optimized reaction conditions are described, from which the combination of tricyclohexylphosphine (Chx3P) and diisopropylazodicarboxylate (DIAD) in THF and R = EWG provides the best results.

Original languageEnglish (US)
Pages (from-to)2513-2515
Number of pages3
JournalOrganic Letters
Volume3
Issue number16
DOIs
StatePublished - Aug 9 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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