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

[41] Discovery of Tetrahydroquinoxalines as Bromodomain and Extra-Terminal Domain (BET) Inhibitors with Selectivity for the Second Bromodomain [J].

Law, Robert P. ;

Atkinson, Stephen J. ;

Bamborough, Paul ;

Chung, Chun-wa ;

Demont, Emmanuel H. ;

Gordon, Laurie J. ;

Lindon, Matthew ;

Prinjha, Rab K. ;

Watson, Allan J. B. ;

Hirst, David J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (10) :4317-4334

[42] A Survey of the Borrowing Hydrogen Approach to the Synthesis of some Pharmaceutically Relevant Intermediates [J].

Leonard, John ;

Blacker, A. John ;

Marsden, Stephen P. ;

Jones, Martin F. ;

Mulholland, Keith R. ;

Newton, Rebecca .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (10) :1400-1410

[43] Organocatalytic enantioselective hetero-Diels-Alder reaction of aldehydes and o-benzoquinone diimide: Synthesis of optically active hydroquinoxalines [J].

Li, Jun-Long ;

Han, Bo ;

Jiang, Kun ;

Du, Wei ;

Chen, Ying-Chun .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (14) :3952-3954

[44] Distinct roles for Ras-guanine nucleotide-releasing factor 1 (Ras-GRF1) and Ras-GRF2 in the induction of long-term potentiation and long-term depression [J].

Li, SM ;

Tian, XJ ;

Hartley, DM ;

Feig, LA .

JOURNAL OF NEUROSCIENCE, 2006, 26 (06) :1721-1729

[45] N-Methylation of Amines with Methanol Catalyzed by a Cp*Ir Complex Bearing a Functional 2,2′-Bibenzimidazole Ligand N [J].

Liang, Ran ;

Li, Shun ;

Wang, Rongzhou ;

Lu, Lei ;

Li, Feng .

ORGANIC LETTERS, 2017, 19 (21) :5790-5793

[46]

Lichosyt D, 2019, NAT CATAL, V2, P114, DOI 10.1038/s41929-018-0207-1

[47]

Lim C. S., 2017, ANGEW CHEM, V129, P7282

[48] Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid [J].

Lim, Ching Si ;

Thanh Truong Quach ;

Zhao, Yu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) :7176-7180

[49] Rhodium-Catalyzed Enantioselective Isomerization of Secondary Allylic Alcohols [J].

Liu, Tang-Lin ;

Ng, Teng Wei ;

Zhao, Yu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (10) :3643-3646

[50] Efficient Cobalt-Catalyzed Methylation of Amines Using Methanol [J].

Liu, Zhenghui ;

Yang, Zhenzhen ;

Yu, Xiaoxiao ;

Zhang, Hongye ;

Yu, Bo ;

Zhao, Yanfei ;

Liu, Zhimin .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (24) :4278-4283

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