Tetrahedron

New synthetic approach to α-fluoro-β-arylvinyl sulfones and their application in Diels–Alder reactions

…, VM Muzalevskiy, ES Balenkova, R Fröhlich, G Haufe

Index: Shastin, Aleksey V.; Nenajdenko, Valentine G.; Muzalevskiy, Vasiliy M.; Balenkova, Elizabeth S.; Froehlich, Roland; Haufe, Guenter Tetrahedron, 2008 , vol. 64, # 41 p. 9725 - 9732

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Citation Number: 16

Abstract

A new pathway towards α-fluoro-β-arylvinyl sulfones was elaborated. The reaction of β- bromo-β-fluorostyrenes with sodium 4-methylphenylsulfinate proceeds with maximum 94: 6 stereoselectivity and 72–90% yields. The formed α-fluoro-β-arylvinyl sulfones were found to be good dienophiles for Diels–Alder reactions with simple 1, 3-dienes. From corresponding (E)-configured dienophiles and cyclopentadiene, cycloadducts bearing the fluorine ...