Issue 8, 2023

Asymmetric synthesis of 7-membered-ring-bridged 3,4-fused tricyclic indoles via Friedel–Crafts alkylation/annulation

Abstract

With N-methyl-4-aminoindole as the 1,4-bisnucleophile, the regio- and enantioselective Friedel–Crafts alkylation/N-hemiacetalization and dehydration sequence with β,γ-unsaturated α-ketoesters was reported using 5 mol% Ni(II)-PyBPI complex, affording diverse chiral 7-membered-ring-bridged 3,4-fused tricyclic indoles in good results (up to 91% yield and 97% ee). The by-products were 6-membered-ring-bridged 4,5-fused tricyclic indoles.

Graphical abstract: Asymmetric synthesis of 7-membered-ring-bridged 3,4-fused tricyclic indoles via Friedel–Crafts alkylation/annulation

Supplementary files

Article information

Article type
Research Article
Submitted
13 Dec. 2022
Accepted
12 Marts 2023
First published
14 Marts 2023

Org. Chem. Front., 2023,10, 1910-1914

Asymmetric synthesis of 7-membered-ring-bridged 3,4-fused tricyclic indoles via Friedel–Crafts alkylation/annulation

B. Xue, C. Hou, X. Wang, M. Xie and H. Guo, Org. Chem. Front., 2023, 10, 1910 DOI: 10.1039/D2QO01982E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements