Synfacts 2011(10): 1083-1083  
DOI: 10.1055/s-0030-1261135
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Purification of Alkene Stereoisomers through Z-Selective Ethenolysis

Contributor(s): Mark Lautens, Stephen G. Newman
S. C. Marinescu, D. S. Levine, Y. Zhao, R. R. Schrock*, A. H. Hoveyda*
Massachusetts Institute of Technology, Cambridge and Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
20 September 2011 (online)

Significance

Many methods exist for preparing disubstituted E-olefins, such as the Horner-­Wadsworth-Emmons reaction and olefin cross-metathesis. While these reactions have proven to be highly reliable and practical, the undesired Z-isomer is often difficult to separate by chromatography or distillation. In the present communication, the authors disclose how pure E-olefins can be obtained from an E/Z mixture through the selective ethenolysis of the Z-isomer.