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

Crowley, Patrick J and Fawcett, John and Griffith, Gerry A and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2005) Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group. Organic and biomolecular chemistry (18). pp. 3297-3310. ISSN 1477-0520

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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.