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01700 am a22002533u 4500 |
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95625 |
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|a dc
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|a Kiesewetter, Elizabeth T.
|e author
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|a Massachusetts Institute of Technology. Department of Chemistry
|e contributor
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|a Schrock, Richard Royce
|e contributor
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|a O'Brien, Robert V.
|e author
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|a Yu, Elsie C.
|e author
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|a Meek, Simon J.
|e author
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|a Hoveyda, Amir H.
|e author
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|a Schrock, Richard Royce
|e author
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|a Synthesis of Z-(Pinacolato)allylboron and Z-(Pinacolato)alkenylboron Compounds through Stereoselective Catalytic Cross-Metathesis
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| 260 |
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|b American Chemical Society (ACS),
|c 2015-02-25T19:21:07Z.
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| 856 |
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|z Get fulltext
|u http://hdl.handle.net/1721.1/95625
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|a 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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|a National Institutes of Health (U.S.) (GM-59426)
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|a National Institutes of Health (U.S.) (GM-47480)
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|a en_US
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|a Article
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|t Journal of the American Chemical Society
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