10.1021/acscatal.7b01912.s001
Tianyu Huang
Tianyu
Huang
Xiaohua Liu
Xiaohua
Liu
Jiawen Lang
Jiawen
Lang
Jian Xu
Jian
Xu
Lili Lin
Lili
Lin
Xiaoming Feng
Xiaoming
Feng
Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines
with Alkynes
American Chemical Society
2017
O 2
enantioselective electrophilic addition
yield
Asymmetric Aerobic Oxidative Cross-Coupling
terminal
oxidation
dioxide
Tetrahydroisoquinoline
Alkyne
intermediate
enantioselectivitie
iminium
bimetallic
alkynyl
formation
oxidant
oxidative
tetrahydroisoquinoline
chiral
alkyne
α-
acetylide
2017-07-25 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Asymmetric_Aerobic_Oxidative_Cross-Coupling_of_Tetrahydroisoquinolines_with_Alkynes/5263066
An
efficient asymmetric aerobic oxidation of tetrahydroisoquinolines
with terminal alkynes was realized under mild reaction conditions
using O<sub>2</sub> as the sole oxidant. A chiral <i>N,N</i>′-dioxide/zinc(II)/iron(II) bimetallic cooperative catalytic
system proves to be efficient for the formation of various α-alkynyl
substituted tetrahydroisoquinolines in good to excellent yields and
enantioselectivities. A primary mechanistic study supports an enantioselective
electrophilic addition of zinc acetylide to the iminium intermediates,
formed through a molecular O<sub>2</sub>-involved oxidative process.