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Ethyl 3-aryl-2-(perfluoroalkanesulfonyl)propenoates were prepared by the Knoevenagel reaction from various aldehydes and ethyl (trifluoromethanesulfonyl)acetate or ethyl (nonafluorobutanesulfonyl)acetate. These deactivated olefins were used in Diels–Alder cycloaddition reactions with cyclopentadiene. The reactions occurred at room temperature to give [4+2] cycloadducts as racemates. The endo stereochemistry of the carboxylic ester and aryl groups was unambiguously assigned by NOE experiments and X-ray analysis.
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Goumont et al. (1999) studied this question.
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