Issue 17, 2006
From the journal:

Organic & Biomolecular Chemistry

A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel–Crafts reactions†

Marco Angeli,a   Marco Bandini,*a   Andrea Garelli,a   Fabio Piccinelli,a   Simona Tommasia  and  Achille Umani-Ronchi*a  

* Corresponding authors

a Dipartimento di Chimica “G. Ciamician”, Università di Bologna, via Selmi 2, Bologna, Italy
E-mail: marco.bandini@unibo.it, achille.umanironchi@unibo.it
Fax: +39-051-2099456

Abstract

A practical catalytic approach to the synthesis of 4-substituted 1,2,3,4-tetrahydro-β-carbolines (THBCs, 1) and 1,2,3,9-tetrahydropyrano[3,4-b]indoles (2) via InBr3-catalyzed intramolecular Friedel–Crafts (F–C) cyclization is described. The use of cross-metathesis reaction represents a direct route to the cyclization precursors and the use of InBr3 (5 mol%) allowed polycyclic indole compounds to be isolated in high yields under mild reaction conditions (rt, DCM, minutes). Finally, efforts toward the development of a stereocontrolled version of the present cyclization are presented, highlighting [salenAlCl] and bimetallic [(salenAlCl)2–InBr3] system as promising chiral Lewis acids (ee up to 60%).

Graphical abstract: A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel–Crafts reactions

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Article information

DOI
https://doi.org/10.1039/B607864H
Article type
Paper
Submitted
02 Jun 2006
Accepted
05 Jul 2006
First published
26 Jul 2006

Org. Biomol. Chem., 2006,4, 3291-3296

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A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel–Crafts reactions

M. Angeli, M. Bandini, A. Garelli, F. Piccinelli, S. Tommasi and A. Umani-Ronchi, Org. Biomol. Chem., 2006, 4, 3291 DOI: 10.1039/B607864H

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