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Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper‐Allenylidenes
Author(s) -
Song Jin,
Zhang ZiJing,
Gong LiuZhu
Publication year - 2017
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.201700105
Subject(s) - annulation , copper , stereoselectivity , lewis acids and bases , chemistry , nucleophile , catalysis , yield (engineering) , ammonium , medicinal chemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , materials science , metallurgy
An asymmetric catalytic decarboxylative [4+2] annulation of 4‐ethynyl dihydrobenzooxazinones and carboxylic acids has been established by cooperative copper and nucleophilic Lewis base catalysis. A C1 ammonium enolate and copper–allenylidene complex, each catalytically generated from different substrates, underwent a cascade asymmetric propargylation and lactamization process to yield optically active 3,4‐dihydroquinolin‐2‐one derivatives with excellent levels of stereoselectivity (up to 99 % ee , 95:5 d.r.).
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