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

被引：20

作者：

Huang, Xian ^{[1
,2
]}

Miao, Maozhong ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 17期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/jo801021f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：6884 / 6887

页数：4