Abstract
The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction.
Keywords
CycloadditionChemistry13-Dipolar cycloadditionCombinatorial chemistryCatalysisArylSolid-phase synthesisCopperYield (engineering)AlkylPeptideAzideOrganic chemistryPolymer chemistryMaterials science
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Publication Info
- Year
- 2002
- Type
- article
- Volume
- 67
- Issue
- 9
- Pages
- 3057-3064
- Citations
- 8319
- Access
- Closed
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Cite This
Christian W. Tornøe,
Caspar Christensen,
Morten Meldal
(2002).
Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides.
The Journal of Organic Chemistry
, 67
(9)
, 3057-3064.
https://doi.org/10.1021/jo011148j
Identifiers
- DOI
- 10.1021/jo011148j