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