Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

Patrick J Crowley; John Fawcett; Gerry A Griffith; Andrew C Moralee; Jonathan Percy; Vittoria Salafia

doi:10.1039/B507131C

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

Patrick J Crowley, John Fawcett, Gerry A Griffith, Andrew C Moralee, Jonathan Percy, Vittoria Salafia

Pure And Applied Chemistry

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Abstract

A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

Original language	English
Pages (from-to)	3297-3310
Number of pages	14
Journal	Organic and biomolecular chemistry
Issue number	18
DOIs	https://doi.org/10.1039/B507131C
Publication status	Published - 2005

Keywords

cyclohexane polyols
Diels–Alder reaction
phenylsulfonyl group

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10.1039/B507131C

Highly functionalised difluorinatedFinal published version, 498 KB

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title = "Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group",

abstract = "A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.",

keywords = "cyclohexane polyols , Diels–Alder reaction , phenylsulfonyl group",

author = "Crowley, {Patrick J} and John Fawcett and Griffith, {Gerry A} and Moralee, {Andrew C} and Jonathan Percy and Vittoria Salafia",

year = "2005",

doi = "10.1039/B507131C",

language = "English",

pages = "3297--3310",

journal = "Organic and biomolecular chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction

T2 - regiochemical control via the phenylsulfonyl group

AU - Crowley, Patrick J

AU - Fawcett, John

AU - Griffith, Gerry A

AU - Moralee, Andrew C

AU - Percy, Jonathan

AU - Salafia, Vittoria

PY - 2005

Y1 - 2005

N2 - A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

AB - A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

KW - cyclohexane polyols

KW - Diels–Alder reaction

KW - phenylsulfonyl group

U2 - 10.1039/B507131C

DO - 10.1039/B507131C

M3 - Article

SN - 1477-0520

SP - 3297

EP - 3310

JO - Organic and biomolecular chemistry

JF - Organic and biomolecular chemistry

IS - 18

ER -

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

Abstract

Keywords

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