Issue 4, 2021

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

Abstract

An exquisite catalytic asymmetric tandem reaction of tertiary enamides catalyzed by a chiral Diph-Pybox/Cu(OTf)2 complex was developed. The method, which comprised an enantioselective intramolecular addition of tertiary enamides to ketonic carbonyls followed by the diastereoselective interception of acyliminium by a tethered indole moiety, enables the expeditious synthesis of indolizino[8,7-b]indole derivatives with high yields, and excellent enantioselectivity and diastereoselectivity.

Graphical abstract: Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

Supplementary files

Article information

Article type
Research Article
Submitted
22 Sep 2020
Accepted
27 Nov 2020
First published
10 Dec 2020

Org. Chem. Front., 2021,8, 721-726

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

X. Xu, M. Xie, J. Li and M. Wang, Org. Chem. Front., 2021, 8, 721 DOI: 10.1039/D0QO01147A

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