New ligands and structural insights into the catalytic asymmetric addition of organozinc reagents to ketones
2011
Huelgas, Gabriela | LaRochelle, Lynne K. | Rivas, Lucrecia | Luchinina, Yekaterina | Toscano, Rubén A. | Carroll, Patrick J. | Walsh, Patrick J. | Anaya de Parrodi, Cecilia
The catalytic asymmetric addition of alkyl groups to ketones has received considerable attention. Outlined herein is the synthesis of two new ligands based on the C₂-symmetric 11,12-diamino-9,10-dihydro-9,10-ethanoanthracene. The scope of the new ligands has been evaluated in the catalytic asymmetric addition of diethylzinc to a variety of ketones. Enantioselectivities as high as 99% have been achieved. The structures of two of these ligands have been determined by X-ray crystallography and are compared with related structures. Additionally, the structure of a titanium complex bound to a bis(sulfonamide) diol ligand is reported.
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