A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines

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

doi:10.1002/anie.201404352

A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines

Alexey Kuznetsov, Anton V. Gulevich, Donald J. Wink, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

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.

Original language	English (US)
Pages (from-to)	9021-9025
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	34
DOIs	https://doi.org/10.1002/anie.201404352
State	Published - Aug 18 2014
Externally published	Yes

Keywords

aminoalkylation
diastereoselectivity
diazo compounds
heterocycles
triazolines

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201404352

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title = "A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-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 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.",

keywords = "aminoalkylation, diastereoselectivity, diazo compounds, heterocycles, triazolines",

author = "Alexey Kuznetsov and Gulevich, {Anton V.} and Wink, {Donald J.} and Vladimir Gevorgyan",

year = "2014",

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doi = "10.1002/anie.201404352",

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T1 - A new reactivity mode for the diazo group

T2 - Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines

AU - Kuznetsov, Alexey

AU - Gulevich, Anton V.

AU - Wink, Donald J.

AU - Gevorgyan, Vladimir

PY - 2014/8/18

Y1 - 2014/8/18

N2 - 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.

AB - 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.

KW - aminoalkylation

KW - diastereoselectivity

KW - diazo compounds

KW - heterocycles

KW - triazolines

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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

Abstract

Keywords

ASJC Scopus subject areas

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