A New Reactivity Mode for the Diazo Group: Diastereoselective 1,3‐Aminoalkylation Reaction of β‐Amino‐α‐Diazoesters To Give Triazolines |
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| Authors: | Alexey Kuznetsov Dr. Anton V. Gulevich Prof. Dr. Donald J. Wink Prof. Dr. Vladimir Gevorgyan |
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| Affiliation: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500 SES, Chicago (USA) http://www.chem.uic.edu/vggroup |
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| Abstract: | 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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| Keywords: | aminoalkylation diastereoselectivity diazo compounds heterocycles triazolines |
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