Heterocycle formation through aza-annulation: A stereochemically controlled route to (±)-lupinine

Article abstract of DOI:10.1016/S0040-4039(00)60550-6

The aza-annulation of an acyclic β-enaminoester with acryloyl chloride was found to be a very efficient method for nitrogen heterocycle formation. Stereospecific hydrogenation of the unsaturated dihydropyridone generated from aza-annulation gave a single disubstituted lactam product. The cis stereochemical relationship of the substituents was confirmed by transformation of the lactam to (±)-lupinine.