Deconstructive isomerization of azetidinols via C–C bond cleavage enabled by N-heterocyclic carbene (NHC) catalysis

Abstract

Herein, we describe an N-heterocyclic carbene (NHC)-catalyzed deconstructive isomerization of azetidinols via an inert C–C bond cleavage. It provides a direct and supplementary pathway to access α-amino ketone and oxazol-2-one derivatives in moderate to good yields. DFT calculation supports the proposed mechanism in which NHC undergoes a concerted proton transfer and ring-opening process. This reaction features non-metal catalysis, simple reaction operation, excellent regioselectivity and gram-scale synthesis.