The Diels–Alder reaction has played a vital role in the development of fields such as synthetic organic chemistry and material design. α-Amido acrylate dienophiles are underutilized substrates for these reactions. Investigations of these dienophiles with both furan and siloxydienes are of particular interest because the products contain synthetically useful substructures that have potential applications in drug delivery and tissue engineering. In order to understand the factors governing the regio- and stereoselectivity of these underdeveloped cyclizations, a computational study was undertaken. Conformational analysis using MMFF in Spartan’18 was performed for the starting materials and products, as well as transition state estimates. Density functional calculations for low energy conformations were also evaluated at the B3LYP 6-31+G(d) level of theory using Gaussian16. The results of this computational study will be described herein.

Computational investigations of α-amido acrylate dienophiles in intermolecular Diels–Alder reactions

ACS Spring Meeting 2021

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