Synthesis of oxaziridines
An efficient and highly enantioselective Payne-type oxidation of N-sulfonyl imines exhibits broad substrate generality and unique chemoselectivity based on the combined use of hydrogen peroxide and trichloroacetonitrile under the catalysis of P-spiro chiral triaminoiminophosphorane.
D. Uraguchi, R. Tsutsumi, T. Ooi, J. Am. Chem. Soc., 2013, 135, 8161-8164.
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.
R. Tsutsumi, S. Kim, D. Uraguchi, T. Ooi, Synthesis, 2014, 46, 871-878.