%0 Generic %A Yang, Yanyan %A Liu, Hongxu %A Peng, Cheng %A Wu, Jie %A Zhang, Jingyi %A Qiao, Yan %A Wang, Xiao-Na %A Chang, Junbiao %D 2016 %T AlCl3‑Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality %U 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/3844044 %R 10.1021/acs.orglett.6b02480.s004 %2 https://acs.figshare.com/ndownloader/files/6010971 %K cycloaddition %K AlCl 3 %K torquoselective 4π- electrocyclic ring opening %K quinone methides %K chromene %K Terminally unsubstituted ynamides %K 6π- electrocyclic ring closure %X A highly torquoselective process for simultaneous control of central and axial chirality by the annulation of terminally substituted ynamides with o-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 with o-quinone methides providing 2-amino-4H-chromenes. %I ACS Publications