N -Sulfonyl α-imino ester-derived chiral oxaziridines: Catalytic asymmetric synthesis and application as a modular chiral organic oxidant

Naoya Tanaka, Ryosuke Tsutsumi, Daisuke Uraguchi, Takashi Ooi

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

A novel class of chiral N-sulfonyl oxaziridines is introduced for use as structurally modifiable chiral oxidants. These oxaziridines are readily prepared from N-sulfonyl α-imino esters in a highly enantioenriched form by oxidation with hydrogen peroxide using l-isoleucine-derived triaminoiminophosphorane as a catalyst. The distinct advantage of their structural modularity is demonstrated through the identification of an optimal oxaziridine that exhibits high reactivity and enantiospecificity in the asymmetric oxidation of a silyl enol ether and N-sulfonyl allylic and homoallylic amines.

Original languageEnglish
Pages (from-to)6999-7002
Number of pages4
JournalChemical Communications
Volume53
Issue number52
DOIs
Publication statusPublished - 2017
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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