Synthesis of Z-(Pinacolato)allylboron and Z-(Pinacolato)alkenylboron Compounds through Stereoselective Catalytic Cross-Metathesis
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Author(s)
Kiesewetter, Elizabeth T.
O’Brien, Robert V.
Yu, Elsie C.
Meek, Simon J.
Hoveyda, Amir H.
Schrock, Richard Royce
Date Issued
April 2013
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Kiesewetter, Elizabeth T., Robert V. O’Brien, Elsie C. Yu, Simon J. Meek, Richard R. Schrock, and Amir H. Hoveyda. “ Synthesis of Z -(Pinacolato)allylboron and Z -(Pinacolato)alkenylboron Compounds through Stereoselective Catalytic Cross-Metathesis .” Journal of the American Chemical Society 135, no. 16 (April 24, 2013): 6026–6029.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja403188t
