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Synfacts 2011(2): 0157-0157
DOI: 10.1055/s-0030-1259250
DOI: 10.1055/s-0030-1259250
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Bicyclononynes: New Ring-Strained Alkynes for Bioorthogonal Labeling
J. Dommerholt, S. Schmidt, R. Temming, L. J. A. Hendriks, F. P. J. T. Rutjes, J. C. M. van Hest, D. J. Lefeber, P. Friedl, F. L. van Delft*
Radboud University Nijmegen, The Netherlands
Further Information
Publication History
Publication Date:
19 January 2011 (online)
Significance
New bicyclo[6.1.0]nonyne (BCN) ring-strained alkynes (e.g. endo- 2) are readily accessible, stable, and exhibit excellent kinetics in metal-free alkyne-azide and alkyne-nitrone cycloadditions (3, 4). The C s symmetry of BCN simplifies NMR analysis and produces a single regioisomer upon cycloaddition.