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A Solid-Supported Organocatalyst for Continuous-Flow Enantioselective Aldol Reactions

Authors

  • Dr. Carles Ayats,

    1. Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans, 16. E-43007, Tarragona (Spain), Fax: (+34) 977-920-222
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  • Andrea H. Henseler,

    1. Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans, 16. E-43007, Tarragona (Spain), Fax: (+34) 977-920-222
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  • Prof. Dr. Miquel A. Pericàs

    Corresponding author
    1. Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans, 16. E-43007, Tarragona (Spain), Fax: (+34) 977-920-222
    2. Departament de Química Orgànica, Universitat de Barcelona, 08028 Barcelona (Spain)
    • Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans, 16. E-43007, Tarragona (Spain), Fax: (+34) 977-920-222
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Abstract

Asymmetric aldol reactions catalyzed by a novel polystyrene-immobilized proline derivative occur in short reaction times with excellent diastereo- and enantioselectivity. The catalyst can be recovered by simple filtration and shows very high reusability. The high activity depicted by the supported catalyst and its chemical and mechanical stability have allowed its application in packed-bed reactors for continuous flow processing. This system can produce enantio- and diastereomerically pure aldol adducts under continuous flow conditions with a residence time of 26 min. Furthermore, the reactor allowed processing of four different aldol products in sequence without any decrease in both catalytic activity and optical purity. The effective catalyst loading could be reduced to 1.6 % (six-fold reduction of catalyst loading compared to the corresponding batch process).

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