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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. |
URI: | http://bura.brunel.ac.uk/handle/2438/13784 |
DOI: | http://dx.doi.org/10.1021/acs.joc.6b01684 |
ISSN: | 0022-3263 |
Appears in Collections: | Dept of Mechanical and Aerospace Engineering Research Papers |
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