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  • Title: Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study.
    Author: Sbai A, Branchadell V, Ortuño RM, Oliva A.
    Journal: J Org Chem; 1997 May 16; 62(10):3049-3054. PubMed ID: 11671684.
    Abstract:
    The Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl(3) have been theoretically studied at the B-LYP/6-31G level. The results obtained show that the catalyst increases both the endo/exo and syn/anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.
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