A New Reactivity Mode for the Diazo Group: Diastereoselective 1, 3‐Aminoalkylation Reaction of β‐Amino‐α‐Diazoesters To Give Triazolines1. Issue 34 (1st July 2014)

• Record Type: Journal Article
• Authors: Kuznetsov, Alexey; Gulevich, Anton V.; Wink, Donald J.; Gevorgyan, Vladimir
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 34(2014)
• Page Start: 9021
• Page End: 9025
• Publication Date: 2014-07-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201404352
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>