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Synlett 2000; 2000(5): 0692-0694
DOI: 10.1055/s-2000-6613
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Synthesis and Reactivity of 4-Silylated Oxazoles

Pascal C. Ducept* , Stephen P. Marsden
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, UK; E-mail: s.marsden@ic.ac.uk
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Publication Date:
31 December 2000 (online)

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Treatment of (triethylsilyl)diazoacetates with rhodium (II) octanoate and a range of substituted nitriles generates trisubstituted oxazoles bearing a triethylsilyl group in the 4-position. Fluoride-mediated desilylation yields 3,5-disubstituted oxazoles, whereas treatment with N-halosuccimides allows the introduction of halogens at the 4-position.

silyl diazoacetate - oxazoles - desilylation - ipso-substitution