Enantioselective Bromocyclization of Tryptamines Induced by Chiral Co(III)-Complex-Templated Bronsted Acids under an Air Atmosphere

被引：30

作者：

Liu, Kun ^{[1
,2
]}

Jiang, Hua-Jie ^{[4
,5
]}

Li, Na ^{[1
,2
]}

Li, Hui ^{[3
]}

Wang, Jing ^{[1
,2
]}

Zhang, Zheng-Zhu ^{[1
,2
]}

Yu, Jie ^{[1
,2
]}

机构：

[1] Anhui Agr Univ, State Key Lab Tea Plant Biol & Utilizat, Hefei 230036, Anhui, Peoples R China

[2] Anhui Agr Univ, Dept Appl Chem, Hefei 230036, Anhui, Peoples R China

[3] Anhui Supervis Inst Vet Drug & Feed, Hefei 230091, Anhui, Peoples R China

[4] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

[5] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 12期

关键词：

COUNTERANION-DIRECTED CATALYSIS; TRANSITION-METAL CATALYSIS; ASYMMETRIC BROMOCYCLIZATION; RECENT PROGRESS; COMPLEXES; ANION; LIGANDS; ALKENES; HALOFUNCTIONALIZATION; BROMOETHERIFICATION;

D O I：

10.1021/acs.joc.8b01196

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral Co(III)-complex-templated Bronsted acids were found to be efficient bifunctional phase-transfer catalysts for the highly enantioselective bromocyclization of protected tryptamines with readily available N-bromosuccinimide (NBS) under an air atmosphere. The 3-bromohexahydropyrrolo[2,3-b]indoles, which are key building blocks of cyclotryptamine alkaloids, were thus obtained in up to 95% yield and 93.5:6.5 er.

引用

页码：6815 / 6823

页数：9

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