Issue 1, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

4-Phenyloxazolidin-2-ones and isoindolin-1-ones: chiral auxiliaries for Diels–Alder reactions of N-substituted 1,3-dienes

Helena McAlonan,a   James P. Murphy,a   Mark Nieuwenhuyzen,a   Karen Reynolds,a   Pakala K. S. Sarma,a   Paul J. Stevenson*a  and  Norris Thompsona  

* Corresponding authors

a School of Chemistry, The Queen's University of Belfast, Belfast, UK

Abstract

Terminally N-substituted dienes derived from 3-methylisoindolin-1-one, 4-isopropyl- and 4-phenyloxazolidin-2-one undergo Diels–Alder reaction with a range of activated dienophiles. The reactions reported are completely regio- and endo-selective, with the diastereoisomeric excess with respect to the auxiliary good to excellent in most of the cases reported. A model has been developed for rationalising the stereochemical outcome of these reactions.

Graphical abstract: 4-Phenyloxazolidin-2-ones and isoindolin-1-ones: chiral auxiliaries for Diels–Alder reactions of N-substituted 1,3-dienes

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Article information

DOI
https://doi.org/10.1039/B108059H
Article type
Paper
Submitted
05 Sep 2001
Accepted
14 Nov 2001
First published
06 Dec 2001

J. Chem. Soc., Perkin Trans. 1, 2002, 69-79

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4-Phenyloxazolidin-2-ones and isoindolin-1-ones: chiral auxiliaries for Diels–Alder reactions of N-substituted 1,3-dienes

H. McAlonan, J. P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. S. Sarma, P. J. Stevenson and N. Thompson, J. Chem. Soc., Perkin Trans. 1, 2002, 69 DOI: 10.1039/B108059H

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