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

The chiral Co­(III)-complex-templated Brønsted 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]...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-06, Vol.83 (12), p.6815-6823
Main Authors: Liu, Kun, Jiang, Hua-Jie, Li, Na, Li, Hui, Wang, Jing, Zhang, Zheng-Zhu, Yu, Jie
Format: Article
Language:English
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Summary:The chiral Co­(III)-complex-templated Brønsted 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01196