Rhodium-Catalyzed Enantioselective Formal [4+1] Cycloaddition of Diazooxindoles and the Danishefsky Diene
Rhodium-Catalyzed Enantioselective Formal [4+1] Cycloaddition of Diazooxindoles and the Danishefsky Diene
复制标题
铑催化的对映选择性缩甲醛[4 1]重氮杂吲哚和达尼舍夫斯基二烯的环加成反应
DOI：
10.1002/ajoc.201700639
复制
发表时间：
2018-02-01
影响因子：
2.7
通讯作者：
Liu, Quan-Zhong
中科院分区：
文献类型：
--
作者：
Cao, Fei;Hu, Fang;Liu, Quan-Zhong
光学富集型环戊酮是一种合成用途广泛的分子，人们非常希望从简单的起始材料中快速、高效、直接地组装它们。在这里，我们报道了一种在Rh催化下重氮氧吲哚和Danishefsky双烯的不对称[4+1]环加成反应。环戊酮的形成是通过环丙烷化原位形成的乙烯基环丙烷的扩环进行的。具有全碳立体中心的光学和高结构富集型吲哚螺环戊酮以良好到优异的产率和对映体选择性(高达90%ee)以一锅两步的方式形成。
Optically enriched cyclopentenones are synthetically versatile molecules, and their rapid and efficient straightforward assembly from simple starting materials is highly desired. Herein, we report a rhodium-catalyzed enantioselective formal [4+1] cycloaddition of diazooxindoles and the Danishefsky diene. The formation of cyclopentenones proceeds via ring expansion of the vinylcyclopropanes formed in situ via cyclopropanation. The optically and highly structurally enriched indoline spirocyclopentenone bearing an all-carbon stereocenter was formed in a one-pot, two-step manner in good to excellent yields and enantioselectivities (up to 90% ee).