Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions

John Fawcett, Gerry A Griffith, Jonathan Percy, Emi Uneyama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Topologically 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.
LanguageEnglish
Pages1277-1280
Number of pages4
JournalOrganic Letters
Volume6
Issue number8
DOIs
Publication statusPublished - 2004

Fingerprint

epoxidation
Epoxidation
Microwave irradiation
epoxy compounds
Epoxy Compounds
Microwaves
hydrolysis
Hydrolysis
microwaves
irradiation
methyl(trifluoromethyl)dioxirane

Keywords

  • difluorinated cyclooctenones
  • stereoselective epoxidations
  • methyl(trifluoromethyl)dioxirane
  • hydrolysis

Cite this

Fawcett, John ; Griffith, Gerry A ; Percy, Jonathan ; Uneyama, Emi. / Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions. In: Organic Letters. 2004 ; Vol. 6, No. 8. pp. 1277-1280 .
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Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions. / Fawcett, John ; Griffith, Gerry A; Percy, Jonathan; Uneyama, Emi.

In: Organic Letters, Vol. 6, No. 8, 2004, p. 1277-1280 .

Research output: Contribution to journalArticle

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T1 - Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions

AU - Fawcett, John

AU - Griffith, Gerry A

AU - Percy, Jonathan

AU - Uneyama, Emi

PY - 2004

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AB - Topologically 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.

KW - difluorinated cyclooctenones

KW - stereoselective epoxidations

KW - methyl(trifluoromethyl)dioxirane

KW - hydrolysis

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