Both octahydroquinoline and 2-azabicyclo[2.2.2]octane heterocycles are important motifs in the synthesis of alkaloid natural products. These valuable architectures can be constructed through intramolecular Diels–Alder reactions of <i>N</i>-substituted oxazolone trienes, and the intermolecular Diels–Alder reactions between α-amido acrylate dienophiles and dihydropyridine-derived dienes, respectively. Computational methods were utilized to explore the factors governing the stereoselectivity of these classes of cycloaddition reactions. Conformational analysis of starting materials, transition state estimates, and products were performed with Spartan’18 using Merck molecular force field (MMFF) and density functional theory (DFT) calculations at the B3LYP 6-31+G(d) level of theory. The resulting low energy conformations for each molecule were evaluated in Gaussian 16 using the M06-2X density functional and transition states were confirmed by intrinsic reaction coordinate (IRC) calculations. The results of this computational investigation will be described and reported herein.

Computational studies of intramolecular and intermolecular Diels–Alder reactions for heterocyclic syntheses

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.