Issue 15, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

Iain Coldham,*a   Katherine M. Crapnell,a   Jonathan D. Moseleyb  and  Rémi Rabota  

* Corresponding authors

a School of Chemistry, University of Exeter, Stocker Road, Exeter, UK

b AstraZeneca Pharmaceuticals, Process R&D Department, Avlon Works, Severn Road, Bristol, UK

Abstract

The aldehyde 2-formyl-2-(pent-4-enyl)-1,3-dithiane 1, containing both alkene and aldehyde functional groups, is a good substrate for intramolecular dipolar cycloaddition reactions after condensation with various N-alkyl α-amino-esters. This paper reports the optimization, scope and stereoselectivity of this reaction to give octahydroindoles (2-azabicyclo[4.3.0]nonanes).

Graphical abstract: Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

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Article information

DOI
https://doi.org/10.1039/B104390K
Article type
Paper
Submitted
18 May 2001
Accepted
21 Jun 2001
First published
10 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1758-1763

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Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

I. Coldham, K. M. Crapnell, J. D. Moseley and R. Rabot, J. Chem. Soc., Perkin Trans. 1, 2001, 1758 DOI: 10.1039/B104390K

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