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.
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.
Huang
Xian
X
Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, People's Republic of China. huangx@mail.hz.zj.cn
Miao
Maozhong
M