Study of a radical cyclizations cascade leading to bicyclo[3.1.1]heptanes
Study of a radical cyclizations cascade leading to bicyclo[3.1.1]heptanes
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DOI：
10.1021/jo981622u
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发表时间：
1999-02-05
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;Fensterbank, L;Malacria, M
涉及 5-exo-dig、1,6-H 转移、6-endo-trig、4-exo-dig 和最终 1,6-H 转移的有效自由基级联允许双环[3.1.1]庚烷的非对映选择性构建。炔丙位置上 R 取代基的大小决定了 6-endo-trig 步骤的非对映选择性。其他参数（炔属取代基、不饱和伙伴等）已被研究，并且级联的范围和局限性已被描述。
An efficient radical cascade involving a 5-exo-dig, a 1,6-H transfer, a 6-endo-trig, a 4-exo-dig, and a final 1,6-H transfer allows the diastereoselective construction of bicyclo[3.1.1]heptanes. The size of the R substituent at the propargylic position governs the diastereoselectivity of the 6-endo-trig step. Other parameters (acetylenic substituents, unsaturated partners, ...) have been investigated, and the scope and the limitations of the cascade have been delineated.