Issue 17, 2004
From the journal:

Organic & Biomolecular Chemistry

Mechanistic studies on the formal aza-Diels–Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions

Stephen Hermitage,a   Judith A. K. Howard,b   David Jay,b   Robin G. Pritchard,c   Michael R. Probertb  and  Andrew Whiting*b  

* Corresponding authors

a GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, UK

b Department of Chemistry, Science Laboratories, University of Durham, South Road, Durham, UK

c Department of Chemistry, U.M.I.S.T., PO Box 88, Manchester, U.K.

Abstract

The reaction of a para-methoxyaniline, ethyl glyoxalate-derived imine with a series of dienes has resulted in products, which initially suggest the operation of different modes of aza-Diels–Alder reaction. However, a more likely explanation is that a common reaction mechanism is operating, involving a step-wise Lewis-acid catalysed process, which only appears to behave similarly to alternative concerted cycloaddition reactions.

Graphical abstract: Mechanistic studies on the formal aza-Diels–Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions

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Article information

DOI
https://doi.org/10.1039/B407293F
Article type
Paper
Submitted
14 May 2004
Accepted
25 Jun 2004
First published
09 Aug 2004

Org. Biomol. Chem., 2004,2, 2451-2460

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Mechanistic studies on the formal aza-Diels–Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions

S. Hermitage, J. A. K. Howard, D. Jay, R. G. Pritchard, M. R. Probert and A. Whiting, Org. Biomol. Chem., 2004, 2, 2451 DOI: 10.1039/B407293F

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