A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines

被引：8

作者：

Zhang, Dan ^{[1
]}

Liu, Junwen ^{[1
]}

Kang, Zhenghui ^{[1
]}

Qiu, Huang ^{[1
]}

Hu, Wenhao ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 46期

基金：

中国国家自然科学基金;

关键词：

C; N-CYCLIC AZOMETHINE IMINES; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; EFFICIENT; PRAZIQUANTEL; ANNULATION; ALDEHYDES; YLIDES; SALTS;

D O I：

10.1039/c9ob02303h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.

引用

页码：9844 / 9848

页数：5

共 52 条

[21] Phosphine-catalyzed [4+3] cycloaddition reaction of aromatic azomethine imines with allenoates [J].

Li, Zhen ;

Yu, Hao ;

Feng, Yalin ;

Hou, Zhanfeng ;

Zhang, Lei ;

Yang, Wenjun ;

Wu, Yang ;

Xiao, Yumei ;

Guo, Hongchao .

RSC ADVANCES, 2015, 5 (43) :34481-34485

[22] Catalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines [J].

Liu, Xihong ;

Wang, Yijie ;

Yang, Dongxu ;

Zhang, Jinlong ;

Liu, Dongsheng ;

Su, Wu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (28) :8100-8103

[23] Three-component reaction of aryl diazoacetates, alcohols, and aldehydes (or imines): Evidence of alcoholic oxonium ylide intermediates [J].

Lu, CD ;

Liu, H ;

Chen, ZY ;

Hu, WH ;

Mi, AQ .

ORGANIC LETTERS, 2005, 7 (01) :83-86

[24] Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines [J].

Mao, Biming ;

Zhang, Junya ;

Xu, Yi ;

Yan, Zhengyang ;

Wang, Wei ;

Wu, Yongjun ;

Sun, Changqing ;

Zheng, Bing ;

Guo, Hongchao .

CHEMICAL COMMUNICATIONS, 2019, 55 (85) :12841-12844

[25] Enantioselective 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines to Unsaturated Nitriles Catalyzed by NiII-Pigiphos [J].

Milosevic, Sandra ;

Togni, Antonio .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9638-9646

[26] Lifitegrast, a Novel Integrin Antagonist for Treatment of Dry Eye Disease [J].

Perez, Victor L. ;

Pflugfelder, Stephen C. ;

Zhang, Steven ;

Shojaei, Amir ;

Haque, Reza .

OCULAR SURFACE, 2016, 14 (02) :207-215

[27] Discovery of a Parenteral Small Molecule Coagulation Factor Xla Inhibitor Clinical Candidate (BMS-962212) [J].

Pinto, Donald J. P. ;

Orwat, Michael J. ;

Smith, Leon M., II ;

Quan, Mimi L. ;

Lam, Patrick Y. S. ;

Rossi, Karen A. ;

Apedo, Atsu ;

Bozarth, Jeffrey M. ;

Wu, Yiming ;

Zheng, Joanna J. ;

Xin, Baomin ;

Toussaint, Nathalie ;

Stetsko, Paul ;

Gudmundsson, Olafur ;

Maxwell, Brad ;

Crain, Earl J. ;

Wong, Pancras C. ;

Lou, Zhen ;

Harper, Timothy W. ;

Chacko, Silvi A. ;

Myers, Joseph E., Jr. ;

Sheriff, Steven ;

Zhang, Huiping ;

Hou, Xiaoping ;

Mathur, Arvind ;

Seiffert, Dietmar A. ;

Wexler, Ruth R. ;

Luettgen, Joseph M. ;

Ewing, William R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (23) :9703-9723

[28] Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition [J].

Qurban, Saira ;

Du, Yu ;

Gong, Jun ;

Lin, Shao-Xia ;

Kang, Qiang .

CHEMICAL COMMUNICATIONS, 2019, 55 (02) :249-252

[29] Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics [J].

Scott, JD ;

Williams, RM .

CHEMICAL REVIEWS, 2002, 102 (05) :1669-1730

[30] The Azomethine Ylide Route to Amine C-H Functionalization: Redox-Versions of Classic Reactions and a Pathway to New Transformations [J].

Seidel, Daniel .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (02) :317-328

← 1 2 3 4 5 6 →