Substrate-controlled selective proximal and distal C-C bond cleavage via Lewis acid mediated O-acylation of 2-(arylmethylene)cyclopropylaldehyde: A stereoselective synthesis of bifunctional methylenecyclobutanes and 1,3-conjugated dienes

摘要

ZnCl2-mediated reactions of (E)-2-(arylmethylene)cyclopropylaldehyde 1 with various acyl chlorides provide a novel method for stereoselective synthesis of bifunctional methlylenecyclobutanes via a proximal-bond cleavage process. Nevertheless, when (Z)-1 was employed, the reactions give 1,3-conjugated dienes through distal-bond cleavage.