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Synfacts 2011(2): 0157-0157  
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

Contributor(s): Timothy M. Swager, Olesya Haze
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
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Publikationsdatum:
19. Januar 2011 (online)

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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.