%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