Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts

被引：18

作者：

Huang, Jian ^{[1
]}

Kong, Han-Han ^{[1
]}

Li, Si-Jia ^{[1
]}

Zhang, Rui-Jin ^{[1
]}

Qian, Hao-Dong ^{[1
]}

Li, Dan-Ran ^{[1
]}

He, Jin-Yu ^{[1
]}

Zheng, Yi-Nuo ^{[1
]}

Xu, Hao ^{[1
]}

机构：

[1] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensing Technol, CCNU uOttawa Joint Res Ctr, Coll Chem,Key Lab Pesticides & Chem Biol,Minist E, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 38期

基金：

中国国家自然科学基金;

关键词：

Amines;

D O I：

10.1039/d1cc00663k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral N,N,P-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.

引用

页码：4674 / 4677

页数：4

共 56 条

[1] Sertraline versus paroxetine in major depression:: Clinical outcome after six months of continuous therapy [J].

Åberg-Wistedt, A ;

Ågren, H ;

Ekselius, L ;

Bengtson, F ;

Åkerblad, AC .

JOURNAL OF CLINICAL PSYCHOPHARMACOLOGY, 2000, 20 (06) :645-652

[2]

[Anonymous], 2015, SYNTHESIS

[3] Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group [J].

Aschwanden, Patrick ;

Stephenson, Corey R. J. ;

Carreira, Erick M. .

ORGANIC LETTERS, 2006, 8 (11) :2437-2440

[4] Copper-Catalyzed Direct Synthesis of Benzamides from Alcohols and Amines [J].

Bantreil, Xavier ;

Fleith, Clement ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMCATCHEM, 2012, 4 (12) :1922-1925

[5] C-N bond forming cross-coupling reactions: an overview [J].

Bariwal, Jitender ;

Van der Eycken, Erik .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303

[6] Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives [J].

Bauer, Eike B. .

SYNTHESIS-STUTTGART, 2012, 44 (08) :1131-1151

[7] Ullmann-Ma Reaction: Development, Scope and Applications in Organic Synthesis† [J].

Cai, Qian ;

Zhou, Wei .

CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (08) :879-893

[8] Asymmetric Catalytic [4+2] Cycloaddition via Cu-Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety [J].

Chen, Hao ;

Lu, Xuehe ;

Xia, Xuejian ;

Zhu, Qiongqiong ;

Song, Yanhong ;

Chen, Jie ;

Cao, Weiguo ;

Wu, Xiaoyu .

ORGANIC LETTERS, 2018, 20 (07) :1760-1763

[9] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[10] Recent advances in well-defined, late transition metal complexes that make and/or break C-N, C-O and C-S bonds [J].

Desnoyer, Addison N. ;

Love, Jennifer A. .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (01) :197-238

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