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J Org Chem. 2018 Jun 15;83(12):6815-6823. doi: 10.1021/acs.joc.8b01196. Epub 2018 May 30.

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

Author information

1
State Key Laboratory of Tea Plant Biology and Utilization and Department of Applied Chemistry , Anhui Agricultural University , Hefei , Anhui 230036 , PR China.
2
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , PR China.
3
Anhui Supervision Institute of Veterinary Drug and Feed , Hefei , Anhui 230091 , PR China.

Abstract

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.

PMID:
29771519
DOI:
10.1021/acs.joc.8b01196

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