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Pyrrolidine-based amino alcohols: novel ligands for the enantioselective alkylation of benzaldehyde

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Detalhes bibliográficos
Resumo: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.
Autores principais:Gonsalves, António M. d'. A. Rocha
Outros Autores:Serra, M. Elisa S.; Murtinho, Dina; Silva, Vitor F.; Beja, A. Matos; Paixão, J. A.; Silva, M. Ramos; Veiga, L. Alte da
Assunto:Enantioselective alkylation [beta]-Amino alcohols Diethylzinc Pyrrolidinoalcohols Benzaldehyde
Ano:2003
País:Portugal
Tipo de documento:artigo
Tipo de acesso:acesso aberto
Instituição associada:Universidade de Coimbra
Idioma:inglês
Origem:Estudo Geral - Universidade de Coimbra
Descrição
Resumo: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.

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