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

页码：1410 / 1414

页数：5

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