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

研究成果: Article査読

31 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1691-1701
ページ数11
ジャーナルTetrahedron
70
8
DOI
出版ステータスPublished - 2014 2月 25
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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