A Mild Method for the Generation and Interception of 1,2-Cycloheptadienes with 1,3-Dipoles
A Mild Method for the Generation and Interception of 1,2-Cycloheptadienes with 1,3-Dipoles
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DOI：
10.1021/acs.orglett.0c02172
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发表时间：
2020-08-07
期刊：
影响因子：
5.2
通讯作者：
West, F. G.
中科院分区：
文献类型：
--
作者：
Almehmadi, Yaseen A.;West, F. G.
1,2-环庚二烯是一种紧张的、短暂的物质，作为一种合成材料尚未得到充分利用。七元环烯以其快速二聚化的倾向而闻名，而关于其与1,3-二烯或1,3-偶极子的环加成反应性的报道相对较少。这项工作描述了1-乙酰氧基-1,2-环庚二烯及其未取代的对偶物的捕获，通过脱硅消除产生，具有一系列1,3偶极捕获伙伴，提供具有高区域选择性和非对映选择性的复杂多环产物。
1,2-Cycloheptadiene is a strained, transient species that has been underutilized as a synthetic building block. Seven-membered cyclic allenes are mostly known for their propensity to undergo rapid dimerization, and relatively little has been reported regarding their cycloaddition reactivity with 1,3-dienes or 1,3-dipoles. This work describes the trapping of 1-acetoxy-1,2-cycloheptadiene and its unsubstituted counterpart, generated via desilylative elimination, with a range of 1,3-dipolar trapping partners, affording complex polycyclic products with high regio- and diastereoselectivity.