An ab initio study of facial selectivity in the Diels-Alder reaction

Research was conducted to examine facial selectivities in the Diels-Alder reactions of five-substituted 1,3-cyclopentadienes with various dienophiles using ab initio calculations. The examination leads to an explanation of the facial selectivity in the reactions of cyclopentadienes that is consistent with all the experimental evidence. Results demonstrate that calculations at the HF/6-31G* level can be reliably used in probing facial selectivity.