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Oxazoles from β-acyloxy-n,n-bis(trimethylsilyl)enamines

✍ Scribed by Robert F. Cunico; Chia P. Kuan

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 225 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)88885-1

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✦ Synopsis

Sequential addition of methyllithium and acyl chlorides to 0-trimethylsflyl acetyltrimethylsilane cyanohydrin affords g-acyloxy-N,N-bis(trimethylsilyl)enamines which cyclize to 2-substituted-4,5-dimethyloxazoles under thermolysis or trimethylsilyl trifluoromethanesulfonate treatment.

Notwithstanding the substantial literature on oxazole chemistry,l preparative efforts in this area continue to be relevant because of the presence of oxazole rings in physiologically active2 and luminescent3 materials and the utility of oxazoles in synthetic methodology.4 Numerous approaches to oxazoles via ring-forming reactions are

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