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Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes
journal contribution
posted on 2017-07-25, 00:00 authored by Tianyu Huang, Xiaohua Liu, Jiawen Lang, Jian Xu, Lili Lin, Xiaoming FengAn
efficient asymmetric aerobic oxidation of tetrahydroisoquinolines
with terminal alkynes was realized under mild reaction conditions
using O2 as the sole oxidant. A chiral N,N′-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 O2-involved oxidative process.
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