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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 11
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Original Articles

SYNTHESIS OF EXOCYCLIC ENAMIDES VIA STEREOCONTROLLED ALLYLIC ISOMERIZATION AND 1,3-TRANSPOSITION

Afzal Khan Department of Chemistry, Queen Mary & Westfield College, Mile End Road, London, E1 4NS, U.K.
,
Charles M. Marson Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H OAJ, U.K.
&
Rod A. Porter
Pages 1753-1764 | Received 22 Sep 1999, Published online: 09 Nov 2006
 
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Abstract

In the presence of pyridinium para-toluenesulfonate (PPTS) an allylic alcohol moiety exocyclic to a lactam ring undergoes allylic isomerisation, or if the solvent is nucleophilic, 1,3- transposition can occur. All the rearrangements occurred with stereocontrol.

ACKNOWLEDGMENTS

We are grateful to the Engineering and Physical Sciences Research Council and SmithKline Beecham for a CASE award (to A.K.).

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