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Synfacts 2010(2): 0181-0181  
DOI: 10.1055/s-0029-1219212
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Metathesis Homocoupling of Terminal Olefins

Contributor(s): Mark Lautens, Chit Tsui
A. J. Jiang, Y. Zhao, R. R. Schrock*, A. H. Hoveyda
Massachusetts Institute of Technology, Cambridge and Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

Highly reactive monoaryloxide-­pyrrolide (MAP) olefin metathesis catalysts of Mo 1 have been prepared from bispyrrolide precursors in situ and employed for enantioselective olefin metathesis reactions. Cross-metatheses with 1 have been found to be Z-selective. The related complexes 2 have also been synthesized and shown to catalyze the Z-selective metathesis of selected internal olefins. The authors report that the principles of Z-selectivity by MAP catalysts can be extended to homocoupling of terminal olefins to form high percentages of Z-homocoupled acyclic products.