Regiocontrol of radical cyclization by Lewis acids. Efficient synthesis of optically active functionalized cyclopentanes and cyclohexanes

被引：28

作者：

Kim, K ^{[1
]}

Okamoto, S ^{[1
]}

Sato, F ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 01期

关键词：

D O I：

10.1021/ol0067890

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of alpha -alkylidenelactones 3a-d with Bu3SnH and a catalytic amount of Et3B effected a 5-exo radical cyclization preferentially to provide the corresponding 1 and 2 in a ratio of 70:30 to 100:0, Meanwhile, the reaction of 3a and 3b in the presence of Et2AlCl proceeded via a B-endo cyclization pathway predominantly to afford 2a and 2b with 90% and 92% regioselectivity, respectively.

引用

页码：67 / 69

页数：3

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