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A New Reactivity Mode for the Diazo Group: Diastereoselective 1,3-Aminoalkylation Reaction of β-Amino-α-Diazoesters To Give Triazolines


  • The support of the NIH (GM-64444) is gratefully acknowledged.


A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.

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