The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation

Ryosuke Tsutsumi, Seonwoo Kim, Daisuke Uraguchi, Takashi Ooi

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

Original languageEnglish
Article number5440
Pages (from-to)871-878
Number of pages8
JournalSynthesis (Germany)
Volume46
Issue number7
DOIs
Publication statusPublished - 2014 Apr
Externally publishedYes

Keywords

  • asymmetric catalysis
  • oxaziridines
  • oxidation
  • peroxides
  • stereoselective synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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