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Induced Chirality in a Metal–Organic Framework by Postsynthetic Modification for Highly Selective Asymmetric Aldol Reactions

Authors

  • Dr. Anneleen L. W. Demuynck,

    1. Center for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee (Belgium), Fax: (+32) 1632 1998
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  • Maarten G. Goesten,

    1. Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)
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  • Enrique V. Ramos-Fernandez,

    1. Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)
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  • Dr. Michiel Dusselier,

    1. Center for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee (Belgium), Fax: (+32) 1632 1998
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  • Prof. Jozef Vanderleyden,

    1. Centre of Microbial and Plant Genetics, KU Leuven, Kasteelpark Arenberg 20, B-3001 Leuven (Belgium)
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  • Prof. Freek Kapteijn,

    1. Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)
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  • Prof. Jorge Gascon,

    Corresponding author
    1. Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)
    • Jorge Gascon, Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)

      Bert F. Sels, Center for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee (Belgium), Fax: (+32) 1632 1998

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  • Prof. Bert F. Sels

    Corresponding author
    1. Center for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee (Belgium), Fax: (+32) 1632 1998
    • Jorge Gascon, Chemical Engineering Department, Catalysis Engineering Section, Delft University of Technology, Julianalaan 136, 2628 BL Delft (The Netherlands)

      Bert F. Sels, Center for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee (Belgium), Fax: (+32) 1632 1998

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Abstract

A straightforward synthetic route to chiral metal–organic frameworks is proposed that relies on an acid–base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.

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