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Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by N-(9-Phenylfluoren-9-yl) β-Amino Alcohols

M. Rita Paleo, Isabel Cabeza and F. Javier Sardina*

*Departamento de Química Orgánica. Facultad de Química. Universidad de Santiago de Compostela. 15706 Santiago de Compostela, Spain, Email: javier.sardinausc.es

M. R. Paleo, I. Cabeza, F. J. Sardina, J. Org. Chem., 2000, 65, 2108-2113.

DOI: 10.1021/jo9917083 (free Supporting Information)


Abstract

N-phenylfluorenyl β-amino alcohols have been evaluated as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. A ligand with a bulky group at the carbinol stereocenter and a small group α to the nitrogen atom displayed the best catalytic activity and enantioselectivity and was used for the addition of diethylzinc to a variety of aromatic and aliphatic aldehydes.

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Key Words

1,2-addition


ID: J42-Y2000