The invention relates to an N-heterocyclic
carbene catalytic functionalized
imine as a novel 1, 4-
dipole synthon and application thereof, and belongs to the field of
chemical synthesis. Under the mild reaction condition, a chiral N-heterocyclic
carbene catalyst is used for catalyzing and activating
aldimine, a novel aza 1, 4-
dipole synthon is obtained under the oxidation condition, and the novel organic
synthon can be further subjected to 4 + 2 cyclization reaction with trifluoroacetophenone,
isatin and an
isatin-derived
imine substrate to generate a
heterocyclic compound with a novel structure and a chiral
quaternary carbon center. According to the method disclosed by the invention, the N-heterocyclic
carbene catalyst with the same chiral configuration and an achiral
thiourea catalyst are used for co-
catalysis, so that three-dimensional diverse synthesis of the trifluoroacetophenone compound can be realized. The method is mild in condition and efficient in reaction and has good substrate universality, and the reported
aldimine-derived 1, 4-aza
dipole synthon provides an important method for synthesizing various functional
nitrogen heterocyclic compounds and has the potential of being applied to industrial production.