Catalytic asymmetric Friedel–Crafts synthesis of 1,1′-diaryl-2-substituted 4-pentenes enables stereoselective access to functionalized tetrahydronaphthalenes

Abstract

A series of electron-rich arenes were reacted with 1-alkyl or 1-aryl 1′-allyl benzylic alcohols to give the corresponding 1,1′-diarylalkanes, in the presence of Lewis and Brønsted acids as catalysts. In the presence of HBF4, 1,1′-diarylalkanes containing an allylic chain were shown to form tetrahydronaphthalenes through a rearrangement involving spirocyclic intermediates. The mechanism of the cyclization is discussed.