5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers.: A highly diastereoselective access to functionalized cyclopentanes
5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers.: A highly diastereoselective access to functionalized cyclopentanes
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DOI：
10.1021/jo9904260
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发表时间：
1999-06-25
影响因子：
3.6
通讯作者：
Malacria, M
中科院分区：
文献类型：
--
作者：
Bogen, S;Gulea, M;Malacria, M
有效的自由基序列包括5-外位转移，非对映选择性1,5- h转移，以及在全碳体系中罕见的5-内三角环化，使得从二异丙基前体1构建具有四个可控立体中心的环戊基衍生物2。烯烃3也作为次要副产物被分离出来。研究了乙基取代基Y的影响，并描述了级联反应的范围和局限性。
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.