Enantioselective Copper-Catalyzed Decarboxylative Propargylic Alkylation of Propargyl β-Ketoesters with a Chiral Ketimine P,N,N-Ligand

被引：112
作者：
Zhu, Fu-Lin [1 ,2 ]
Zou, Yuan [1 ]
Zhang, De-Yang [1 ,2 ]
Wang, Ya-Hui [1 ]
Hu, Xin-Hu [1 ]
Chen, Song [1 ]
Xu, Jie [1 ]
Hu, Xiang-Ping [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 05期
关键词：
alkylation; asymmetric catalysis; copper; ligand design; synthetic methods; SUBSTITUTION-REACTIONS; CONJUGATE ADDITION; TERMINAL ALKYNES; KETO-ESTERS; AMINATION; AMINES; HYDROGENOLYSIS; COMPLEXES; ACETATES; SCOPE;
D O I：
10.1002/anie.201309182
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first enantioselective copper-catalyzed decarboxylative propargylic alkylation has been developed. Treatment of propargyl beta-ketoesters with a catalyst, prepared in situ from [Cu(CH3CN)(4)BF4] and a newly developed chiral tridentate ketimine P,N,N-ligand under mild reaction conditions, generates beta-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 beta-ethynyl ketones in a highly enantioenriched form.
引用
收藏
页码：1410 / 1414
页数：5
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