Catalytic conversion of diazocarbonyl compounds to imines: applications to the synthesis of tetrahydropyrimidines and β-lactams.

The synthesis of α-carbonylimines by rhodium(II)-catalyzed reactions of α-diazoesters and organic azides has been developed and applied in hetero-Diels-Alder reactions to form highly functionalized tetrahydropyrimidines and in a one-pot, multicomponent transformation between aryldiazoacetates, p-anisyl azide, and an enonediazoacetate to produce β-lactams in high yields and diastereoselectivities.