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Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed
Anthony Labelle1, Bruce A Arndtsen1
1Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada. bruce.arndtsen@mcgill.ca.
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.
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