Diels-Alder Reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene.
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.
Department of Chemistry, Imperial College London , South Kensington, SW7 2AZ, United Kingdom.
Hossay
H
Abas
Wolfson Centre for Materials Processing, Brunel University , Kingston Lane, Uxbridge, UB8 3PH, United Kingdom.
Christopher S
CS
Frampton
Department of Chemistry, Imperial College London , South Kensington, SW7 2AZ, United Kingdom.
Alan C
AC
Spivey