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New ligands and structural insights into the catalytic asymmetric addition of organozinc reagents to ketones |
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| Authors: | Gabriela HuelgasLynne K LaRochelle Lucrecia RivasYekaterina Luchinina Rubén A ToscanoPatrick J Carroll Patrick J WalshCecilia Anaya de Parrodi |
| Institution: | a Departamento de Ciencias Químico Biológicas, Universidad de las Américas Puebla, Santa Catarina Mártir s/n, Cholula, 72820 Puebla, Mexico b Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, México c Department of Chemistry, University of Pennsylvania, 231 S. 34th St, Philadelphia, PA 19104, USA |
| Abstract: | 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. |
| Keywords: | Ketone Alkylation Asymmetric Catalysis Alcohols Homogeneous Catalysis |
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