Jump to main content
Jump to site search

Issue 46, 2020
Previous Article Next Article

Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines

Author affiliations

Abstract

Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- or 3-substituted indoles to non-activated aziridine-2-carboxaldehydes in dioxane afforded 2-(indol-3-ylhydroxymethyl)aziridines whose ring opening with various nucleophiles rendered multi-substituted tryptamine derivatives. The reaction of the same aziridine-2-carboxaldehyde with three moles of indole in dichloromethane yielded tris-indole adducts β-(3,3′-bisindolyl)methyl (BIM) tryptamines from sequential steps including nucleophilic addition to aldehyde, Michael type Friedel–Crafts alkylation of the mono-adduct followed by regio- and stereoselective ring-opening of the aziridine ring.

Graphical abstract: Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines

Back to tab navigation

Supplementary files

Article information


Submitted
09 Sep 2020
Accepted
29 Oct 2020
First published
30 Oct 2020

Org. Biomol. Chem., 2020,18, 9473-9482
Article type
Paper

Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines

L. Macha, D. Singh, H. Rhee and H. Ha, Org. Biomol. Chem., 2020, 18, 9473
DOI: 10.1039/D0OB01865A

Social activity

Search articles by author

Spotlight

Advertisements