A synthetic method for the intermolecular Diels–Alder reaction between α-amido acrylate dienophiles with cyclic dienes described by Spivey <i>et al</i>. afforded mixtures of <i>endo/exo</i> products. In order to increase the reaction’s utility and to understand the factors governing stereoselectivity, a computational study was undertaken to identify a method of analysis consistent with synthetic experiments. Conformational analysis (MMFF) was carried out for relevant species using Spartan’16. Low energy conformations were subsequently evaluated using density functional theory calculations at the B3LYP 6-31G(d) level of theory using Gaussian 09. The results of this computational study and comparison to experimental results will be described.

Computational studies of intermolecular Diels–Alder reactions of α-amido acrylates

256th National Meeting (2018)

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