Chelation-controlled stereospecific ring-opening arylation of α-aminoaryl-tethered alkylidenecyclopropanes: stereoselective synthesis of polysubstituted conjugated dienes

Abstract

Conjugated dienes are vital due to their presence in natural products, bioactive molecules and functional materials as well as their wide synthetic applications. Herein, we report a palladium-catalyzed stereospecific ring-opening arylation of α-aminoaryl-tethered alkylidenecyclopropanes for the stereoselective synthesis of 1,1,2-trisubstituted conjugated dienes. This method features excellent functional group tolerance (including ether, thioether, halogen, aldehyde, cyano, ester, ketone, trifluoromethoxy and alkenyl), a good substrate scope (35 examples), and high regio- and stereoselectivity.