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
09 Ndz 2020
Accepted
29 Nhl 2020
First published
30 Nhl 2020

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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