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Alkene Chemoselectivity in Ruthenium-Catalyzed Z-Selective Olefin Metathesis

Authors

  • Dr. Jeffrey S. Cannon,

    1. Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • Prof. Robert H. Grubbs

    Corresponding author
    1. Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
    • Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)===

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  • This work was financially supported by the NIH (R01GM031332 and N.R.S.A. to J.S.C.: F32GM103002), and the NSF (CHE-1212767). NMR spectra were obtained by instruments supported by the NIH (RR027690). Materia Inc. is acknowledged for the generous donation of metathesis catalysts 1, 2, 5, and 6.

Abstract

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Chelated ruthenium catalysts can facilitate highly chemoselective olefin metathesis. Terminal and internal Z olefins reacted selectively to form new Z olefins in the presence of internal E olefins. Chemoselectivity for terminal olefins was also observed over both sterically hindered and electronically deactivated alkenes.

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