A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
Chunrui Sun, Bowman Potter and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu
C. Sun, B. Potter, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 6534-6537.
DOI: 10.1021/ja500029w (free Supporting Information)
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In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates with high levels of asymmetric induction. Mechanistic experiments suggest that the reaction occurs by a stereochemistry-determining transmetalation with inversion of configuration at carbon.
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B. Potter, A. A. Szymaniak, E. K. Edelstein, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 17918-17921.