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Synfacts 2011(9): 0979-0979  
DOI: 10.1055/s-0030-1261036
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Z-Selective Ruthenium-Catalyzed Olefin Cross Metathesis

Contributor(s): Mark Lautens, Stephen G. Newman
K. Endo, R. H. Grubbs*
California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Olefin cross-metathesis has found widespread use in bench-scale and process chemistry as a reliable way of forming carbon-­carbon double bonds (see Review below). With few exceptions, the more thermodynamically ­favored E-isomers are produced. The authors demonstrate that, by utilizing a novel chelated ­ruthenium catalyst, selectivity for the Z-isomer can be achieved.

Review: G. C. Vougioukalakis, R. H. Grubbs Chem. Rev. 2010, 110, 1746-1787.