abstract
The synthetic method recently established by Spivey and co-workers describes the intermolecular Diels–Alder reactions between α-aminoacrylate(s) dienophiles and cyclic dienes. These reactions gave stereoisomeric mixtures of endo and exo products. A computational study was undertaken in an effort to identify a method of analysis that would yield results similar to those of the synthetic experiments. Starting materials, transition state estimates, and products were subjected to conformational analysis (MMFF) using the Spartan molecular modeling program (Spartan’16). The low-energy conformations produced for each molecule were subjected to density functional theory calculations at the B3LYP 6-31+G(d) level of theory using the Gaussian09 program. The results of this computational study are described. These calculations provide information about molecular geometry and energy values of the reaction that will be compared with the experimental results in an effort to verify whether computational analysis supports the stereoselectivity observed in physical experimentation.
