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

Research output: Contribution to journalArticle

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244 Downloads (Pure)

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 languageEnglish
Pages (from-to)3297-3310
Number of pages14
JournalOrganic and biomolecular chemistry
Issue number18
DOIs
Publication statusPublished - 2005

Fingerprint

reaction control
Furans
Cycloaddition
Cycloaddition Reaction
cyclohexane
Chlorides
Ions
furans
cycloaddition
chlorides
rings
products
ions
polyol
cyclohexene
Cyclohexane

Keywords

  • cyclohexane polyols
  • Diels–Alder reaction
  • phenylsulfonyl group

Cite this

Crowley, Patrick J ; Fawcett, John ; Griffith, Gerry A ; Moralee, Andrew C ; Percy, Jonathan ; Salafia, Vittoria. / Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group. In: Organic and biomolecular chemistry. 2005 ; No. 18. pp. 3297-3310.
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Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group. / Crowley, Patrick J; Fawcett, John; Griffith, Gerry A; Moralee, Andrew C; Percy, Jonathan; Salafia, Vittoria.

In: Organic and biomolecular chemistry, No. 18, 2005, p. 3297-3310.

Research output: Contribution to journalArticle

TY - JOUR

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

SP - 3297

EP - 3310

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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