5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers.: A highly diastereoselective access to functionalized cyclopentanes

被引：55

作者：

Bogen, S ^{[1
]}

Gulea, M ^{[1
]}

Fensterbank, L ^{[1
]}

Malacria, M ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Lab Chim Organ Sunth, F-75252 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 13期

关键词：

D O I：

10.1021/jo9904260

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient radical sequence involving a 5-exo-dig, a diastereoselective 1,5-H transfer, and a rarely observed in an all-carbon system 5-endo-trig cyclization allows the construction of cyclopentyl derivatives 2 bearing four controlled stereogenic centers from diisopropyl precursors 1. Olefins 3 were also isolated as minor side products. The effect of the acetylenic substituent Y has been investigated, and the scope and the limitations of the cascade have been delineated.

引用

页码：4920 / 4925

页数：6

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