Asymmetric synthesis of nitrogen heterocycles by reaction of chiral β-enaminocarbonyl substrates with acrylate derivatives

We have studied the reactivity of β-enaminoesters 1 (R2=OMe) or β-enaminoketone 1 (R2=Me), derived from (S)-phenylglycinol, with activated acrylate derivatives. Substrates 1 (R1=Me) afforded by aza-annulation oxazololactams 2 and 3,4-dihydro-2-pyridones 3. In the same conditions β-enaminoesters 1 (R1=H) furnish N-acylated oxazolidines 4.