Stereoconvergent, Redox-Neutral Access to Tetrahydroquinoxalines through Relay Epoxide Opening/Amination of Alcohols

被引：47

作者：

Xu, Guangda ^{[1
]}

Yang, Guoqiang ^{[2
]}

Wang, Yue ^{[1
]}

Shao, Pan-Lin ^{[2
]}

Yau, Jia Ning Nicolette ^{[2
]}

Liu, Bing ^{[1
]}

Zhao, Yunbo ^{[1
]}

Sun, Ye ^{[1
]}

Xie, Xinxin ^{[1
]}

Wang, Shuo ^{[1
]}

Zhang, Yao ^{[1
]}

Xia, Lixin ^{[1
]}

Zhao, Yu ^{[2
]}

机构：

[1] Liaoning Univ, Coll Chem, Shenyang 110036, Liaoning, Peoples R China

[2] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 40期

关键词：

borrowing hydrogen catalysis; enantioselectivity; redox-neutral catalysis; relay catalysis; tetrahydroquinoxaline; RUTHENIUM-CATALYZED SYNTHESIS; DIASTEREODIVERGENT ALPHA-ALLYLATION; METHODOLOGY COOPERATIVE CATALYSIS; IR/ZN DUAL CATALYSIS; ASTERISK-IR COMPLEX; BORROWING HYDROGEN; ASYMMETRIC HYDROGENATION; N-METHYLATION; ENANTIOSELECTIVE HYDROGENATION; ENANTIOPURE AMINES;

D O I：

10.1002/anie.201906199

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present an economical catalytic procedure to convert readily available 1,2-diaminobenzenes and terminal epoxides into valuable 1,2,3,4-tetrahydroquinoxalines in a highly enantioselective fashion. This procedure operates through relay zinc and iridium catalysis, and achieves redox-neutral and stereoconvergent production of valuable chiral heterocycles from racemic starting materials with water as the only side product. The use of commercially available reagents and catalysts and a convenient procedure also make this catalytic method attractive for practical application.

引用

页码：14082 / 14088

页数：7

共 101 条

[1]

[Anonymous], 2011, ANGEW CHEM, V123, P3887

[2]

[Anonymous], 2016, ANGEW CHEM, V128, P872

[3]

[Anonymous], 2018, Angew. Chem, V130, P474

[4]

[Anonymous], 2014, ANGEW CHEM, V126, P1423

[5]

[Anonymous], 2014, Angew. Chem, V126, P9294

[6] Asymmetric Hydrogenation of Quinoxalines, Benzoxazines, and a Benzothiazine Catalyzed by Chiral Ruthenabicyclic Complexes [J].

Arai, Noriyoshi ;

Saruwatari, Yu ;

Isobe, Kotaro ;

Ohkuma, Takeshi .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) :2769-2774

[7] The Catalytic Amination of Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Neubert, Lorenz ;

Zhang, Min ;

Neumann, Helfried ;

Beller, Matthias .

CHEMCATCHEM, 2011, 3 (12) :1853-1864

[8] Use of an Iridium-Catalyzed Redox-Neutral Alcohol-Amine Coupling on Kilogram Scale for the Synthesis of a GlyT1 Inhibitor [J].

Berliner, Martin A. ;

Dubant, Stephane P. A. ;

Makowski, Teresa ;

Ng, Karl ;

Sitter, Barbara ;

Wager, Carrie ;

Zhang, Yinsheng .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (05) :1052-1062

[9] Enantioselective hydrogenation of 2-methylquinoxaline to (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline by iridium catalysis [J].

Bianchini, C ;

Barbaro, P ;

Scapacci, G ;

Farnetti, E ;

Graziani, M .

ORGANOMETALLICS, 1998, 17 (15) :3308-3310

[10] Iridium-Difluorphos-Catalyzed Asymmetric Hydrogenation of 2-Alkyl- and 2-Aryl-Substituted Quinoxalines: A General and Efficient Route into Tetrahydroquinoxalines [J].

Cartigny, Damien ;

Nagano, Takuto ;

Ayad, Tahar ;

Genet, Jean-Pierre ;

Ohshima, Takashi ;

Mashima, Kazushi ;

Ratovelomanana-Vidal, Virginie .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :1886-1891

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