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A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of ?-amino-?-diazoesters to give triazolines.

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 ?-amino-?-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.

SUBMITTER: Kuznetsov A

PROVIDER: S-EPMC4157640 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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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.

Kuznetsov Alexey A Gulevich Anton V AV Wink Donald J DJ Gevorgyan Vladimir V

Angewandte Chemie (International ed. in English) 20140701 34

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 ...[more]

PMID: 24986811

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