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|Title:||Diels-Alder reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene|
|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.|
|Appears in Collections:||Dept of Mechanical Aerospace and Civil Engineering Research Papers|
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