Enantioselective Synthesis of Sulfinamidines via Asymmetric Nitrogen Transfer from N-H Oxaziridines to Sulfenamides

Sulfinamidines are promising aza-SIV chiral building blocks in asymmetric synthesis and drug discovery. However, no report has documented their enantioselective synthesis. Here we present an enantioselective synthesis of sulfinamidines via electrophilic amination of sulfenamides using an enantiopure N-H oxaziridine. The resulting enantiomerically enriched primary sulfinamidines are configurationally stable at 90 degrees C in solution and show remarkable stability against organic acids and bases under non-aqueous conditions. We also demonstrate a one-pot, three-component, enantioselective synthesis of sulfinamides using N-H oxaziridine reagents. Herein is reported an enantioselective synthesis of sulfinamidines by electrophilic amination of sulfenamides with enantiopure N-H oxaziridines. The enantioenriched sulfinamidines show remarkable chemical and configurational stability against high temperature, acids, and bases in non-aqueous solution. One-pot, three-component, enantioselective synthesis of sulfinamides is further demonstrated by employing enantiopure N-H oxaziridine reagents. image