Issue 46, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
21 محرم 1442
Accepted
12 ربيع الأول 1442
First published
13 ربيع الأول 1442

Org. Biomol. Chem., 2020,18, 9473-9482

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

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