Stereoselective synthesis of C-sulfonylated aziridines from halomethyl phenyl sulfone and N-tert-butanesulfinyl imines

Abstract

A highly efficient and stereoselective synthesis of C-sulfonylated aziridines is developed by using a one-step aza-Darzens reaction. When sodium bis(trimethylsilyl)amide (NaHMDS) was used as the base, bromomethyl phenyl sulfone reacted with N-tert-butanesulfinyl imines to afford the 2-sulfonylated aziridine products in very good yields and with stereoselectivities up to 50 : 1.