Fluoropropenoates as dienophiles in the Diels–Alder reaction

Journal of Fluorine Chemistry(2006)

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Abstract
Several fluorinated alkenes were prepared from known ethyl (R)-2-fluoro-4,5-dihydroxyisopropylidine-2-pentenoate (1). The fluoroalkenoates were tested as dienophiles with several dienes and showed cycloaddition only with the very reactive diene, 1,3-diphenylisobenzofuran (5). Fluorobutenolide 2 reacted with 5 to produce the endo-syn adduct 9 in a highly stereoselective manner.
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Key words
Diels–Alder,Fluoroalkene,Cycloaddition
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