Issue 7, 2019
From the journal:

Organic Chemistry Frontiers

Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence†

Chao-Chao Xie,a   Rui Tanb  and  Yan-Kai Liu ORCID logo *ac  

* Corresponding authors

a Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
E-mail: liuyankai@ouc.edu.cn

b School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, China

c Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, China

Abstract

An organocatalysis triggered highly regio- and stereoselective two-step sequence between hemiacetals and indole-containing nitroolefins was developed. The key to the success of this sequence was the intramolecular oxocarbenium ion induced collective alkylation at the C3, C2, or N1-position of the indole moiety, respectively, providing biologically important polycyclic indole derivatives with different ring connectivities. An unexpected epimerization was observed during the C3-alkylation process, which generated products with different relative configurations compared with the C2- and N1-alkylation products.

Graphical abstract: Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence

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Article information

DOI
https://doi.org/10.1039/C8QO01406J
Article type
Research Article
Submitted
25 Dec 2018
Accepted
08 Feb 2019
First published
12 Feb 2019

Org. Chem. Front., 2019,6, 919-924

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Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence

C. Xie, R. Tan and Y. Liu, Org. Chem. Front., 2019, 6, 919 DOI: 10.1039/C8QO01406J

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