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

Kuznetsov Alexey | Zendy; Gulevich Anton V. | Zendy; Wink Donald J. | Zendy; Gevorgyan Vladimir | Zendy

Premium

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

Author(s) -

Kuznetsov Alexey,

Gulevich Anton V.,

Wink Donald J.,

Gevorgyan Vladimir

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201404352

Subject(s) - chemistry , diazo , reactivity (psychology) , intramolecular force , functional group , nucleophile , electrophile , group (periodic table) , medicinal chemistry , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , polymer

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research