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The Practical Preparation of Chiral N-Sulfonyl Oxaziridines via Catalytic Asymmetric Payne Oxidation

Ryosuke Tsutsumi, Seonwoo Kim, Daisuke Uraguchi, Takashi Ooi*

*Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan, Email: tooiapchem.nagoya-u.ac.jp

R. Tsutsumi, S. Kim, D. Uraguchi, T. Ooi, Synthesis, 2014, 46, 871-878.

DOI: 10.1055/s-0033-1340818 (free Supporting Information)


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Abstract

The asymmetric Payne oxidation of N-sulfonyl aldimines catalyzed by a P-spiro chiral triaminoiminophosphorane enables a practical synthesis of optically active N-sulfonyl oxaziridines with high efficiency and an excellent level of enantioselectivity. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

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Key Words

asymmetric organocatalysis, oxaziridines, oxidation, hydrogen peroxide, stereoselective synthesis


ID: J66-Y2014