Sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to biscyclopropane-fused tetralins

Abstract

Efficient tBuOK-mediated sequential condensation and double desulfonylative cyclopropanation of readily accessible 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins is described. This high-yielding, single-step strategy provides a variety of polysubstituted biscyclopropane-fused tetralins with six contiguous stereogenic centers via the construction of five carbon–carbon single bonds. A plausible mechanism is proposed and discussed. In the overall reaction process, water and sulfinic acid salts were generated as the byproducts.