Rhodium-catalyzed intermolecular [3+3] cycloaddition of vinyl aziridines with C,N-cyclic azomethine imines: stereospecific synthesis of chiral fused tricyclic 1,2,4-hexahydrotriazines

Abstract

An atom-economic route to ring-fused 1,2,4-hexahydrotriazines relying upon a new synthetic application of vinylaziridines in a rhodium-catalyzed intermolecular [3+3] cycloaddition of C,N-cyclic azomethine imines has been reported. Highly efficient chirality transfer in the present transformation was also observed, providing a new method for the synthesis of sp³-carbon-rich 1,2,4-hexahydrotriazines in an enantioselective manner.