This is a repository copy of Inter- and intramolecular Diels-Alder/retro-Diels-Alder reactions of 4-silylated oxazoles . White Rose Research Online URL for this paper: http://eprints.whiterose.ac.uk/925/ Article: Ducept, P.C. and Marsden, S.P. (2002) Inter- and intramolecular Diels-Alder/retro-Diels-Alder reactions of 4-silylated oxazoles. Arkivoc, 2002 (6). pp. 22-34. ISSN 1424-6376 Reuse See Attached Takedown If you consider content in White Rose Research Online to be in breach of UK law, please notify us by emailing
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[email protected] https://eprints.whiterose.ac.uk/ Issue in Honor of Prof. Charles W. Rees ARKIVOC 2002 (vi) 22 -34 Inter- and intramolecular Diels-Alder/retro-Diels-Alder reactions of 4-silylated oxazoles Pascal C. Ducepta and Stephen P. Marsden*,a,b a) Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U. K. b) Current address: Department of Chemistry, University of Leeds, Leeds LS2 9JT, U. K. E-mail:
[email protected] Dedicated to Professor Charles Rees F.R.S. on the occasion of his 75th birthday Abstract 4-Silylated oxazoles have been shown to undergo inter- and intramolecular Diels-Alder/retro- Diels-Alder reactions with electron-poor alkynes to generate polysubstituted furans. The ease of synthesis of the requisite oxazoles by the rhodium-catalysed condensation of nitriles with silylated diazoacetate greatly increases the scope of this reaction. Keywords: Silylated oxazoles, diazoacetate, furans, Diels-Alder, retro-Diels-Alder.