Sulfur Ylide Mediated Asymmetric Synthesis of Aziridines from Sulfinylketimines

Significance

An asymmetric synthesis of aziridine derivatives with high diastereoselectivity from the base-mediated reaction of chiral sulfinyl­ketimines with an allylic sulfur ylide is reported. While good yields and diastereoselectivities of asymmetric aziridinations of sulfinylaldimines with dimethylsulfonium methylide (Corey-Chaykovsky conditions) were previously observed (D. Morton, D. Pearson, R. A. Stockman Synlett 2003, 1985-1988), in the present study, sulfinylketimines were shown not to be suitable substrates for the transformation under the same reaction conditions. However, using the less basic ylide derived from (S)-allyl tetrahydrothiophenium bromide, successful reactions with improved yields were achieved for a reasonably wide range of substrates.