The role of the planar chirality of iron tricarbonyl substituted homochiral amino alcohols in the asymmetric alkylation of aldehydes with diethylzinc |
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| Institution: | 1. FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal,;2. LAQV, REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal,;3. Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland;4. Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, Brazil |
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| Abstract: | Homochiral amino alcohols bearing an iron tricarbonyl moiety were prepared from 2-amino-1,1-diphenylethanol derivatives 4a–d and (3S,4S)-η4,7-octa-4,6-dien-3-ol]Fe(CO)3 complex 2. The addition of diethylzinc to aldehydes bearing electron donating substituents in the presence of these chiral ligands gave the alkylated products in good enantiomeric excess (up to 93% e.e.), whereas the addition to aldehydes bearing electron withdrawing substituents resulted in low yields and poor enantiomeric excesses. |
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