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Org Lett. 2014 Feb 7;16(3):740-3. doi: 10.1021/ol403427s. Epub 2014 Jan 14.

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

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  • 1Department of Chemistry & Biochemistry, University of Maryland , College Park, Maryland 20742, United States.


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.

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