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

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.

Key words

asymmetric catalysis - oxaziridines - oxidation - peroxides - stereoselective synthesis

• References

• 1 Present address: Department of Chemistry, Seoul National University, Seoul 151-747, Republic of Korea.

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