Organocatalytic [3+2] Annulation of β-Tetralones with α,β-Unsaturated Aldehydes

Abstract

AbstractThe NBS-mediated organocatalytic cascade synthesis of 4,5-dihydronaphtho[2,1-b]furan-1-carbaldehydes from α,β-unsaturated aldehydes and 2-tetralones have been developed. In this synthesis strategy, the C1 of in situ generated brominated 2-tetralone was used as identical twin electron donor–acceptor, and the Cβ and Cα of enals were used as the heterogeneous twin electron acceptor–donors. The process has been realized by a synergistic amine/p-TSA catalyzed one-pot cascade Michael addition–cyclopropanation–ring opening–oxa-Michael addition under mild conditions and without the use of transition metals.