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

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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 AlCl3 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.
Original languageEnglish
Pages (from-to)3049-3054
JournalJournal of Organic Chemistry
Volume62
Issue number10
DOIs
Publication statusPublished - 1 Dec 1997

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