Asymmetric Diels–Alder reaction of heterocyclic o-quinodimethane with 2-arylidene-1,3-indanedoines to access tetrahydrospirocarbazole-indanediones via trienamine intermediate

Abstract

Enantioselective Diels–Alder reaction of in situ generated heterocyclic quinodimethane from indolylacrylaldehyde with arylidine-1,3-indanedinones is carried out in the presence of chiral prolinol-derived catalysts. The reaction proceeds through a trienamine pathway, resulting in chiral tetrahydrospirocarbazoles-indane-1,3-diones. The reaction proceeds with high to excellent enantio- and diasteroselectivities with excellent yields.