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Imines derived from enantiopure trans-3-amino-azetidin-2-ones as dienophiles in aza-Diels-Alder reactions with activated and nonactivated dienes

Beta-lactams are increasingly being used as synthons for the synthesis of variety of natural products. Efforts have been made in exploring such new aspects of beta-lactam chemistry using enantiomerically pure beta-lactams as versatile intermediates for the synthesis of aromatic beta-amino acids and their derivatives, oligopeptides, labelled peptides and azetidines, which are further converted to polyamines, polyamino alcohols, amino sugars and polyamino ethers. On the other hand, six-membered nitrogen heterocycles, pyridines and pyridones, represent the key building units in medicinal chemistry and interesting intermediates in organic synthesis. They are found in natural alkaloids, which possess strong pharmacological activity, peptides and aza-sugars.

beta-Lactam; Imine; Diels-Alder reaction; Lewis acid

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