Sept 2016 - Article in J. Org. Chem. Published

Hossay's paper on Diels-Alder reactions of alpha-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene is published in J. Org. Chem.

Hossay Abbas, Christopher J. Frampton and Alan C. Spivey, 'Diels-Alder reactions of α-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene', J. Org. Chem. 2016, 81, 9947–9956; DOI: 10.1021/acs.joc.6b01684

Thermal Diels-Alder reactions of α-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene have been explored to investigate the factors influencing the endo/exo selectivity.

For the dihydropyridine, steric factors allowed the diastereoselectivity to be modulated to favor either endo- or exo-ester adducts. For cyclopentadiene, the endo-ester adducts were favored regardless of steric perturbation, although catalysis by bulky Lewis acids increased the proportion of exo-ester adducts in some cases. These Lewis acids were incompatible with the dihydropyridine diene as they induced its decomposition.