AlCl<sub>3</sub>‑Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality Yanyan Yang Hongxu Liu Cheng Peng Jie Wu Jingyi Zhang Yan Qiao Xiao-Na Wang Junbiao Chang 10.1021/acs.orglett.6b02480.s003 https://acs.figshare.com/articles/dataset/AlCl_sub_3_sub_Catalyzed_Annulations_of_Ynamides_Involving_a_Torquoselective_Process_for_the_Simultaneous_Control_of_Central_and_Axial_Chirality/3844047 A highly torquoselective process for simultaneous control of central and axial chirality by the annulation of terminally substituted ynamides with <i>o</i>-quinone methides is reported. In the presence of AlCl<sub>3</sub>, 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-2<i>H</i>-chromenes. Terminally unsubstituted ynamides undergo AlCl<sub>3</sub>-catalyzed [4 + 2] cycloaddition with <i>o</i>-quinone methides providing 2-amino-4<i>H</i>-chromenes. 2016-09-21 17:22:30 cycloaddition AlCl 3 torquoselective 4π- electrocyclic ring opening quinone methides chromene Terminally unsubstituted ynamides 6π- electrocyclic ring closure