Journal of the Chemical Society. Perkin transactions I p. 1319 - 1321 (1996)
Update date:2022-09-26
Topics:
Jones, Raymond C. F.
Dunn, Stephen H.
Duller, Kathryn A. M.
Cycloaddition of oxygen-functionalized nitrite oxides to the enamine from ethyl acetoacetate produces 4-ethoxycarbonyl-5-methylisoxazoles carrying a 3-tetrahydropyranyloxymethyl, 3-diethoxymethyl or 3-ethoxycarbonyl substituent; the 3-formylisoxazole is prepared from the former two and condensed in situ with phosphoranes to give 3-alkenylisoxazoles that are cleaved by hexacarbonylmolybdenum or hydrogenolysis to afford α-alkoxycarbonyl-β-diketones.
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