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Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones
Author(s) -
Li Xinyao,
Großkopf Johannes,
Jandl Christian,
Bach Thorsten
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013276
Subject(s) - intramolecular force , enantioselective synthesis , cycloaddition , olefin fiber , chemistry , intermolecular force , absolute configuration , imine , catalysis , aryl , substrate (aquarium) , yield (engineering) , hydrogen bond , medicinal chemistry , stereochemistry , organic chemistry , molecule , materials science , geology , metallurgy , alkyl , oceanography
3‐Substituted quinoxalin‐2(1 H )‐ones and various aryl‐substituted or tethered olefins underwent an enantioselective, inter‐ or intramolecular aza Paternò–Büchi reaction upon irradiation at λ =420 nm in the presence of a chiral sensitizer (10 mol %). For the intermolecular reaction with 1‐arylethenes as olefin components, the scope of the reaction was studied (14 examples, 50–99 % yield, 86–98 % ee ). The absolute and relative configuration of the products were elucidated by single‐crystal X‐ray crystallography. The reaction is suggested to occur by triplet energy transfer in a hydrogen‐bonded 1:1 complex between the imine substrate and the catalyst. The intramolecular cycloaddition, consecutive reactions of the product azetidines, and an alternative reaction mode of quinoxalinones were investigated in preliminary experiments.