Issue 18, 2005
From the journal:

Organic & Biomolecular Chemistry

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

Patrick J. Crowley,a   John Fawcett,b   Gerry A. Griffith,b   Andrew C. Moralee,b   Jonathan M. Percy*b  and  Vittoria Salafiab  

* Corresponding authors

a Syngenta Ltd., Jealott's Hill International Research Centre, Bracknell, Berkshire, UK

b Department of Chemistry, University of Leicester, University Road, Leicester, UK
E-mail: jmp29@le.ac.uk
Fax: +44 116 252 3789
Tel: +44 116 252 2140

Abstract

A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts which could 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.

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

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Article information

DOI
https://doi.org/10.1039/B507131C
Article type
Paper
Submitted
20 May 2005
Accepted
20 Jul 2005
First published
11 Aug 2005

Org. Biomol. Chem., 2005,3, 3297-3310

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

P. J. Crowley, J. Fawcett, G. A. Griffith, A. C. Moralee, J. M. Percy and V. Salafia, Org. Biomol. Chem., 2005, 3, 3297 DOI: 10.1039/B507131C

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