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Rhodium‐Catalyzed Enantioselective Formal [4+1] Cycloaddition of Diazooxindoles and the Danishefsky Diene
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2018-01-19 , DOI: 10.1002/ajoc.201700639
Fei Cao 1 , Fang Hu 1 , Qi-Mei Xie 1 , Gao-Ya Luo 1 , Wen-Dao Chu 1 , Long He 1 , Quan-Zhong Liu 1
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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).

中文翻译:

铑催化的重氮吲哚和Danisheefsky Diene的对映选择性形式[4 + 1]环加成反应

光学富集的环戊烯酮是合成上通用的分子,因此非常需要它们从简单的起始原料快速而有效地直接组装。在本文中,我们报道了重氮基吲哚和Danishefsky二烯的铑催化对映选择性形式[4 + 1]环加成反应。环戊烯酮的形成通过经由环丙烷化原位形成的乙烯基环丙烷的扩环而进行。光学和高度结构富集的带有全碳立构中心的二氢吲哚螺环戊烯酮以单罐,两步方式形成,具有良好的产率和优异的对映选择性(最高90%ee)。
更新日期:2018-01-19
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