Although the application of cationic aluminum complexes in catalysis has been extensively investigated, the incorporation of aluminum cation into chiral environment is less explored. In this work, a C2-symmetric chiral tetra-coordinate aluminum cation [3][X] bearing two prolinol-derived ligands were prepared from commercially available starting materials in two steps. The high Lewis acidity of [3][X] exceeding that of B(C6F5)3 was verified by a  competition binding experiment. Preliminary catalytic activity studies of [3][X] revealed that the tetra-coordinate aluminum cation is effective in accomplishing high conversion in all cases. Furthermore, high enantioselectivity was observed in catalytic reactions involving a,b-unsaturated ketones. To further explore the possibilities of aluminum cation in catalyzing challenging transformation such as asymmetric olefin reduction, a series of C2-symmetric chiral alkyl tri-coordinate aluminum cations bearing aryl-substituted bisoxazoline ligands [(BOX)Al][X] were successfully generated. These highly Lewis acidic complexes were found to be active in catalytic olefin functionalization.

Chiral Aluminum Cation in Catalysis

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