Abstract
Fluorinated alcohols increase the rates and endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (−)-menthyl and (−)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (−)-menthyl acrylate, but decreases it when the dienophile is (−)-8-phenylmenthyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.
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