Synthesis of Z-(Pinacolato)allylboron and Z-(Pinacolato)alkenylboron Compounds through Stereoselective Catalytic Cross-Metathesis
Journal of the American Chemical Society2013Vol. 135(16), pp. 6026–6029
Citations Over TimeTop 10% of 2013 papers
Elizabeth T. Kiesewetter, Robert V. O’Brien, Elsie C. Yu, Simon J. Meek, Richard R. Schrock, Amir H. Hoveyda
Abstract
The first examples of catalytic cross-metathesis (CM) reactions that furnish Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds are disclosed. Products are generated with high Z selectivity by the use of a W-based monoaryloxide pyrrolide (MAP) complex (up to 91% yield and >98:2 Z:E). The more sterically demanding Z-alkenylboron species are obtained in the presence of Mo-based MAP complexes in up to 93% yield and 97% Z selectivity. Z-selective CM with 1,3-dienes and aryl olefins are reported for the first time. The utility of the approach, in combination with catalytic cross coupling, is demonstrated by a concise and stereoselective synthesis of anticancer agent combretastatin A-4.
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