AlCl3-Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality
AlCl3-Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality
复制标题
AlCl3 催化的酰胺成环涉及同时控制中心和轴向手性的扭矩选择过程
DOI：
10.1021/acs.orglett.6b02480
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发表时间：
2016
期刊：
影响因子：
5.2
通讯作者：
Chang Junbiao
中科院分区：
文献类型：
--
作者：
Yang Yanyan;Liu Hongxu;Peng Cheng;Wu Jie;Zhang Jingyi;Qiao Yan;Wang Xiao-Na;Chang Junbiao
A highly torquoselective process for simultaneous control of central and axial chirality by the annulation of terminally substituted ynamides witho-quinone methides is reported. In the presence of AlCl3, a sequence comprising a [2 + 2] cycloaddition followed by the torquoselective 4π-electrocyclic ring opening and 6π-electrocyclic ring closure leads to highly stereoselective formation of diastereoisomeric 4-amino-2H-chromenes. Terminally unsubstituted ynamides undergo AlCl3-catalyzed [4 + 2] cycloaddition witho-quinone methides providing 2-amino-4H-chromenes.
