Chiral aziridination of olefins using a chiral sulfanamide as the nitrogen source

Article abstract of DOI:10.1055/s-0029-1218545

Chiral aziridination of cyclic a-bromoenones is achieved by the use of the lithium salt of (S_s)-(+)-p-toluenesulfinamide, which leads to products with diastereomeric excesses in the range of 30-65% using a simple protocol. A key factor associated with chiral induction is the incorporation of the reacting olefin in a cycle, indicating the importance of conformational restriction in the reacting double bond. Georg Thieme Verlag Stuttgart.