Iron-catalyzed cascade C-C/C-O bond formation of 2,4-dienals with donor-acceptor cyclopropanes: access to functionalized hexahydrocyclopentapyrans.

Abstract

Iron-catalyzed cascade C-C and C-O bond formation of 2,4-dienals with donor-acceptor cyclopropanes (DACs) has been developed to furnish hexahydrocyclopentapyrans. Optically active DACs can be coupled stereospecifically (>97% ee). Chirality transfer, use of iron-catalysis and substrate scope are the salient practical features.