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 Mar 2023
First published
14 Mar 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

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