Premium
Enantioselective Copper‐Catalyzed Decarboxylative Propargylic Alkylation of Propargyl β‐Ketoesters with a Chiral Ketimine P,N,N‐Ligand
Author(s) -
Zhu FuLin,
Zou Yuan,
Zhang DeYang,
Wang YaHui,
Hu XinHu,
Chen Song,
Xu Jie,
Hu XiangPing
Publication year - 2014
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.201309182
Subject(s) - enantioselective synthesis , propargyl , alkylation , chemistry , ligand (biochemistry) , ketone , catalysis , chiral ligand , copper , combinatorial chemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
The first enantioselective copper‐catalyzed decarboxylative propargylic alkylation has been developed. Treatment of propargyl β‐ketoesters with a catalyst, prepared in situ from [Cu(CH 3 CN) 4 BF 4 ] and a newly developed chiral tridentate ketimine P,N,N‐ligand under mild reaction conditions, generates β‐ethynyl ketones in good yields and with high enantioselectivities without requiring the pregeneration of ketone enolates. This new process provides facile access to a range of chiral β‐ethynyl ketones in a highly enantioenriched form.