Highly stereoselective 6π electrocyclization of bridged bicyclic 1,3,5-trienes
Highly stereoselective 6π electrocyclization of bridged bicyclic 1,3,5-trienes
复制标题
DOI：
10.1021/ol070924s
复制
发表时间：
2007-06-21
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：
Benson, Chantel L.;West, F. G.
包裹在桥联双环骨架中的共轭 1,3,5-己三烯通过交叉偶联和所得二烯的半还原来制备。三烯在环境温度或升高的温度下经历6π电环化以提供复杂的多环环己二烯。在所有情况下，与相应的 4 pi Nazarov 环化相比，都看到了有利于从桥联双环系统的 exo 面进行环化的完全选择性。
Conjugated 1,3,5-hexatrienes encased in bridged bicyclic skeletons are prepared by cross-coupling followed by half-reduction of the resulting dienynes. The trienes undergo 6 pi electrocyclization at an ambient or elevated temperature to furnish complex, polycyclic cyclohexadienes. In all cases, complete selectivity in favor of cyclization from the exo face of the bridged bicyclic system was seen, in contrast to the corresponding 4 pi Nazarov cyclizations.