Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition

Jun Cai Meng, Valery V. Fokin, M. G. Finn

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.

Original languageEnglish
Pages (from-to)4543-4546
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number27
DOIs
Publication statusPublished - 4 Jul 2005
Externally publishedYes

Fingerprint

Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Copper
Gems
Ligands
Kinetics
Enantioselectivity
Catalysis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition. / Meng, Jun Cai; Fokin, Valery V.; Finn, M. G.

In: Tetrahedron Letters, Vol. 46, No. 27, 04.07.2005, p. 4543-4546.

Research output: Contribution to journalArticle

Meng, Jun Cai ; Fokin, Valery V. ; Finn, M. G. / Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 27. pp. 4543-4546.
@article{8fbede77d5e54762bbb39ec2f4cb357c,
title = "Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition",
abstract = "The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.",
author = "Meng, {Jun Cai} and Fokin, {Valery V.} and Finn, {M. G.}",
year = "2005",
month = "7",
day = "4",
doi = "10.1016/j.tetlet.2005.05.019",
language = "English",
volume = "46",
pages = "4543--4546",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "27",

}

TY - JOUR

T1 - Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition

AU - Meng, Jun Cai

AU - Fokin, Valery V.

AU - Finn, M. G.

PY - 2005/7/4

Y1 - 2005/7/4

N2 - The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.

AB - The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.

UR - http://www.scopus.com/inward/record.url?scp=20344406206&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=20344406206&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.05.019

DO - 10.1016/j.tetlet.2005.05.019

M3 - Article

VL - 46

SP - 4543

EP - 4546

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -