Abstract:
Aza-annulation of enamines generated from β-ketoester using maleic and itaconic
anhydrides produces functionalized γ- and δ-lactams with good diastereoselectivity.
Subsequent hydrolysis of the aza-annulation products yielded dicarboxylic acids, which are
susceptible to further decarboxylation. Simultaneous migration of the C=C double bond occurs
during the decarboxylation of β-γ unsaturated carboxylic acids with an electron-rich enamide
double bond. This provides a straightforward synthesis route towards 1,2,3,4-
tetrahydropyridine-2-ones and 3-pyrrolin-2-ones.