Highly-functionalised difluorinated cyclohexane polyols via the Diels-Alder reaction: regiochemical control via the phenylsulfonyl group.
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 E1(C)B or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.
Crowley
Patrick J
PJ
Syngenta Ltd., Jealott's Hill International Research Centre, Bracknell, Berkshire, UK RG42 6EY.
Fawcett
John
J
Griffith
Gerry A
GA
Moralee
Andrew C
AC
Percy
Jonathan M
JM
Salafia
Vittoria
V