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
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.
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页码:4920 / 4925
页数:6
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