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Title: Diels-Alder reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene
Authors: Abas, H
Frampton, CS
Spivey, AC
Issue Date: 2016
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry, 81(20): pp. 9947−9956, (2016)
Abstract: 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.
ISSN: 0022-3263
Appears in Collections:Dept of Mechanical Aerospace and Civil Engineering Research Papers

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