Pyrrolidine-based amino alcohols: novel ligands for the enantioselective alkyla...

• Author(s): Gonsalves, António M. d'. A. Rocha ; Serra, M. Elisa S. ; Murtinho, Dina ; Silva, Vitor F. ; Beja, A. Matos ; Paixão, J. A. ; Silva, M. Ramos ; Veiga, L. Alte da
• Date: 2003
• Persistent ID: http://hdl.handle.net/10316/5168
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): Enantioselective alkylation; [beta]-Amino alcohols; Diethylzinc; Pyrrolidinoalcohols; Benzaldehyde
• Document Type: Article
• Language: English

Description

A series of easily obtained pyrrolidine-based [beta]-amino alcohols derived from tartaric acid and primary amines was synthesized and used as chiral ligands in the enantioselective alkylation of benzaldehyde. Using diethylzinc, 1-phenyl-1-propanol was obtained with enantiomeric excesses of up to 80% when (3S,4S)-N-(1-naphthylmethyl)-3,4-dihydroxypyrrolidine was used. The nature of the N-substituent on the ligand, as well as the reaction temperature proved to significantly influence reaction product distribution as well as the enantiomeric excess of the chiral alcohol. http://www.sciencedirect.com/science/article/B6TGM-4790515-2/1/7b585f37987962e55a30bf6583ce3e06