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Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation.

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The chiral weakly coordinating (3,3'-biphenyl-BINOL)BF2 anion can be generated by the reaction of the BINOL derivative with Cu(NCMe)4BF4. Structural analysis suggest the anion is weakly coordinating to Cu+. However, its… Click to show full abstract

The chiral weakly coordinating (3,3'-biphenyl-BINOL)BF2 anion can be generated by the reaction of the BINOL derivative with Cu(NCMe)4BF4. Structural analysis suggest the anion is weakly coordinating to Cu+. However, its use in cyclopropanation reactions leads to the rearrangement of the anion to create a chiral 3,3'-diphenyl-BINOL ligand that coordinates to copper. The latter suggests an important feature to consider when using weakly association anions, but can also be used to design simple chiral BINOL-based ligands for asymmetric cyclopropanation.

Keywords: based borate; binol; cyclopropanation; binol based; anion; chiral binol

Journal Title: Chemical communications
Year Published: 2022

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