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Creators/Authors contains: "Biscoe, Mark R"

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  1. ; ; ; (, Chemical Science)
    Stereospecific Pd-catalyzed cross-coupling reactions using enantioenriched benzylic tricyclohexyltin nucleophiles enable broad access to enantioenriched benzylic stereocenters. 
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  2. ; ; ; ; (, Organic Letters)
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  3. ; ; ; ; (, ACS Catalysis)
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  4. ; ; (, Nature Reviews Chemistry)
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  5. ; (, Organometallics)
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  6. ; ; ; ; ; ; ; (, Chem)
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  7. ; ; ; ; (, Angewandte Chemie International Edition)
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  8. ; ; ; ; ; (, Science)
    Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed. 
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