2 research outputs found
Diels–Alder Reactions of α‑Amido Acrylates with <i>N</i>‑Cbz-1,2-dihydropyridine and Cyclopentadiene
Thermal Diels–Alder reactions
of α-amido acrylates
with <i>N</i>-Cbz-1,2-dihydropyridine and cyclopentadiene
have been explored to investigate the factors influencing the <i>endo/exo</i> selectivity. For the dihydropyridine, steric factors
allowed the diastereoselectivity to be modulated to favor either <i>endo-</i> or <i>exo-</i>ester adducts. For cyclopentadiene,
the <i>endo</i>-ester adducts were favored regardless of
steric perturbation, although catalysis by bulky Lewis acids increased
the proportion of <i>exo</i>-ester adducts in some cases.
These Lewis acids were incompatible with the dihydropyridine diene
as they induced its decomposition