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

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Abstract

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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Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

B. Potter, A. A. Szymaniak, E. K. Edelstein, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 17918-17921.

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Key Words

Suzuki coupling, alkylation, benzylboronates

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ID: J48-Y2014