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

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

doi:10.1021/ol0496327

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

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

18 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.

Original language	English
Pages (from-to)	1277-1280
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	8
DOIs	https://doi.org/10.1021/ol0496327
Publication status	Published - 2004

Keywords

difluorinated cyclooctenones
stereoselective epoxidations
methyl(trifluoromethyl)dioxirane
hydrolysis

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10.1021/ol0496327

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title = "Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions",

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.",

keywords = "difluorinated cyclooctenones, stereoselective epoxidations, methyl(trifluoromethyl)dioxirane, hydrolysis",

author = "John Fawcett and Griffith, {Gerry A} and Jonathan Percy and Emi Uneyama",

year = "2004",

doi = "10.1021/ol0496327",

language = "English",

volume = "6",

pages = "1277--1280 ",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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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

Y1 - 2004

N2 - 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.

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

U2 - 10.1021/ol0496327

DO - 10.1021/ol0496327

M3 - Article

SN - 1523-7060

VL - 6

SP - 1277

EP - 1280

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

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

Abstract

Keywords

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