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.
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1 Dec 1997|