Asymmetric epoxidation of α-substituted acroleins catalyzed by diphenylprolinol silyl ether

Bojan P. Bondzic, Tatsuya Urushima, Hayato Ishikawa, Yujiro Hayashi

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Asymmetric epoxidation of α-substituted acroleins with hydrogen peroxide has been catalyzed by diphenylprolinol diphenylmethylsilyl ether to afford α-substituted-β,β-unsubstituted-α,β-epoxy aldehyde with excellent enantioselectivity and the generation of a chiral quaternary carbon center. The method was applied to a short synthesis of (R)-methyl palmoxirate.

Original languageEnglish
Pages (from-to)5434-5437
Number of pages4
JournalOrganic letters
Volume12
Issue number23
DOIs
Publication statusPublished - 2010 Dec 3
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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