Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines?
Organic & Biomolecular Chemistry Pub Date: 2020-10-30 DOI: 10.1039/D0OB01865A
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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