Organic Chemistry

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Authors

Abstract

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Non-symmetrical ynehydrazides could be obtained in 25-97% yield using azaglycine derivatives as nucleophiles. The transfor-mation is compatible with most functional groups naturally occurring on amino acid side-chains and allows the transfer of silyl-, alkyl- and aryl-substituted alkynes. The obtained α-alkynyl azaglycine products could be further functionalized by nucleophilic attack or cycloaddition on the triple bond.

Version notes

Conditions to hydrolyze the hydrazone on functionalized products were added in Scheme 4. The experimental procedure and characterization data for this reaction were added to the SI, and a cover page was added to the SI.

Content

Thumbnail image of Azapeptide alkynylation vfinal2.pdf

Supplementary material

Thumbnail image of azapeptideSI-withspectravf.pdf
Supporting Information
Experimental procedures, characterization data and copy of NMR spectra.