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

Abdelouahid Sbai; Vicenç Branchadell; Rosa Maria Ortuño; Antonio Oliva

doi:10.1021/jo960447j

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

J Org Chem. 1997 May 16;62(10):3049-3054. doi: 10.1021/jo960447j.

Authors

Abdelouahid Sbai¹, Vicenç Branchadell, Rosa Maria Ortuño, Antonio Oliva

Affiliation

¹ Departament de Química, Universitat Autònoma de Barcelona, Edifici Cn, 08193 Bellaterra, Spain.

PMID: 11671684
DOI: 10.1021/jo960447j

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.