Novel Polystyrene-Immobilized Chiral Amino Alcohols as Heterogeneous Ligands for the Enantioselective Arylation of Aldehydes in Batch and Continuous Flow Regime

    José AugustoForni, Luiz Fernando Toneto, Novaes, Renan Galaverna, Julio C.Pastre

    • Institute of Chemistry, University of Campinas – UNICAMP, PO Box 6154, 13083-970, Campinas, SP, Brazil

    Six different ligands derived from (S)-proline, (2S,4R)-4-hydroxyproline, (S)-tyrosine and (S)-phenylalanine were synthesized and screened in homogeneous phase for the enantioselective arylation of aldehydes using mixed organozinc reagents. The best ligands were immobilized on the Merrifield resin and evaluated in batch and continuous flow regimes. In batch, up to 89% yield and 90:10 enantiomeric ratio were obtained. In continuous flow regime, we explored the examples that were more challenging in batch, being able to obtain the desired product in 88% yield and 94:6 of enantiomeric excess in residence time as low as 1.5 min.

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