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Biotinylated Metathesis Catalysts: Synthesis and Performance in Ring Closing Metathesis

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Abstract

Nine biotinylated Grubbs–Hoveyda and Grubbs-type metathesis catalysts were synthesized and evaluated in ring closing metathesis reactions of N-tosyl diallylamine and 5-hydroxy-2-vinylphenyl acrylate. Their catalytic activity in organic- and aqueous solvents was compared with the second generation Grubbs–Hoveyda catalyst. The position of the biotin-moiety on the N-heterocyclic carbene was found to critically influence the catalytic activity of the corresponding ruthenium-based catalysts.

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Acknowledgments

The authors thank The Seventh Framework Programme Project METACODE (KBBE, “Code-engineered new-to-nature microbial cell factories for novel and safety enhanced bio-production”) as well as ITN BioChemLig (FP7-ITN-238434) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, University of Basel, Spitalstrasse 51, 4056, Basel, Switzerland

    Anna Kajetanowicz, Anamitra Chatterjee, Raphael Reuter & Thomas R. Ward

Authors
  1. Anna Kajetanowicz
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  2. Anamitra Chatterjee
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  3. Raphael Reuter
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  4. Thomas R. Ward
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Corresponding author

Correspondence to Thomas R. Ward.

Additional information

Anna Kajetanowicz and Anamitra Chatterjee have contributed equally to the work.

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Kajetanowicz, A., Chatterjee, A., Reuter, R. et al. Biotinylated Metathesis Catalysts: Synthesis and Performance in Ring Closing Metathesis. Catal Lett 144, 373–379 (2014). https://doi.org/10.1007/s10562-013-1179-z

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  • DOI: https://doi.org/10.1007/s10562-013-1179-z

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