Asymmetric synthesis of 4,5-dihydropyrrole derivatives via DKR: DROC of activated aziridines with enaminones

Abstract

We present a practical, efficient and highly enantioselective route to 4,5-dihydropyrrole derivatives via DKR assisted DROC of racemic aziridines with N,N-dimethyl enaminones employing Cu(I)-(S)-XylBINAP as the catalyst system. The strategy works successfully with a wider substitution patterns producing a library of 4,5-dihydropyrroles with excellent yields (up to 96%) and excellent enantiomeric excess (ee up to 97%). The application of the DKR concept in DROC of aziridines is reported for the first time.