Catalytic asymmetric Payne oxidation under the catalysis of P-spiro chiral triaminoiminophosphorane: Application to the synthesis of N-sulfonyl oxaziridines

Daisuke Uraguchi, Ryosuke Tsutsumi, Takashi Ooi

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

The studies on the development of a highly enantioselective oxidation of N-sulfonyl imines with hydrogen peroxide-trichloroacetonitrile system utilizing P-spiro chiral triaminoiminophosphoranes as an organic base catalyst are detailed. This method is general and scalable, and exhibits unique chemoselectivity, providing a practical stereoselective route to structurally diverse N-sulfonyl oxaziridines. The mechanistic investigations reveal that the reaction proceeds through the Payne-type oxidation pathway. The synthetic utility of the optically active N-sulfonyl oxaziridines as versatile organic oxidants and chiral building blocks is also demonstrated.

Original languageEnglish
Pages (from-to)1691-1701
Number of pages11
JournalTetrahedron
Volume70
Issue number8
DOIs
Publication statusPublished - 2014 Feb 25
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Hydrogen peroxide
  • Imine
  • Organocatalysis
  • Oxaziridine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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