| 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 alkynesto azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, andan azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions werefully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis ismild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structureof 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipolesentering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols wereprepared by the Mitsunobu reaction.
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