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 sep 2020
Accepted
29 okt 2020
First published
30 okt 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements