Synthetic Study of Nitrogen Containing Compounds Based on New Reaction Mechanisms Using Alkynyl Imines as Starting Material

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Chiral phosphoric acid catalyzed enantioselective reduction of iminocyclobutenones prepared from alkynyl imines was carried out to give the chiral aminocyclobutenones with high enantioselectivities. Thermal rearrangement of chiral aminocyclobutenones in the presence of appropriate amines proceeded to afford the chiral cis- ortrans-β-lactams with high diastereo- and enantioselectivities, respectively. Moreover, thermal rearrangement of iminocyclobutenones gave the 4-quinolones in high yields.