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

摘要

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 AICI_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.