Studies On The Stereoselectivity In Diels-Alder Reaction Of Cyclopentadiene With Acrylic And Methacrylic Ester

In this dissertation, the three kinds of asymmetric Diels-Alder reaction were introduced. The preparation of bornyl acrylate and bornyl methacrylate catalyzed by nanometer solid superacids were studied. The stereoselectivity in Diels-Alder reaction of cyclopentadiene with acrylic and methacrylic ester were also studied.Firstly, using nanometer solid superacids as the catalyst, the esterification reaction of borneol with arylic and methacrylic acid could proceed smoothly. The effects of reaction time, reaction temperature, the molar ratio of acid to borneol, the use level of catalyst on esterification reaction were discussed, and the optical reaction conditions were obtained. We also studied the reuse and the revivification of the catalyst S₂O₈^2-/ZrO₂. The boiling point of the product was tested. The structure of the product was characterized by IR, 1H NMR and 13C NMR spectra.Secondly, we researched the asymmetric Diels-Alder reaction of cyclopentadiene with chiral bornyl acrylate, which was prepared by the chiral auxiliary nature borneol. The corresponding acid or alcohol were obtained after the Diels-Alder adduct were hydrolyzed or disoxidated. The effect of reaction tempertature, catalyst or noncatalyst on Diels-alder reaction were discussed.Thirdly, we researched the stereoselectivity of Diels-Alder reaction between the different methacrylic ester and cyclopentadiene. The yield and the endo/exo ratios of the product under different conditions were studied. We also preliminarily inferred the possible reason that the endo/exo ratios were changed on the presence of catalyst.