Unexpectedly Selective Formation and Reactions of Epoxycyclooctenones under Microwave-Mediated Conditions
2004; American Chemical Society; Volume: 6; Issue: 8 Linguagem: Inglês
10.1021/ol0496327
ISSN1523-7060
AutoresJohn Fawcett, Gerry A. Griffith, Jonathan M. Percy, E. Uneyama,
Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoTopologically mobile difluorinated cyclooctenones undergo rapid, high-yielding, and completely stereoselective epoxidations with methyl(trifluoromethyl)dioxirane. The epoxides resist conventional hydrolysis but react smoothly in basic media under microwave irradiation to afford unique hemiacetals and hemiaminals in good yield. [reaction: see text]
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