Postsynthetic Modification of a Metal–Organic Framework (MOF) Structure for Enantioselective Catalytic Epoxidation

Authors

  • Dr. Natalia Candu,

    1. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
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  • Dr. Mădălina Tudorache,

    1. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
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  • Dr. Mihaela Florea,

    1. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
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  • Dr. Elena Ilyes,

    1. Faculty of Chemistry, “Babes-Bolyai” University, RO-400028 Cluj-Napoca (Romania)
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  • Dr. Florin Vasiliu,

    1. National Institute of Materials Physics, Str. Atomistilor 105b, 077125 Magurele-Ilfov (Romania)
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  • Ionel Mercioniu,

    1. National Institute of Materials Physics, Str. Atomistilor 105b, 077125 Magurele-Ilfov (Romania)
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  • Prof. Dr. Simona M. Coman,

    Corresponding author
    1. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
    • Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
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  • Prof. Dr. Ionel Haiduc,

    1. Faculty of Chemistry, “Babes-Bolyai” University, RO-400028 Cluj-Napoca (Romania)
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  • Prof. Dr. Marius Andruh,

    1. Laboratory of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, Str. Dumbrava Rosie 23, 020464 Bucharest (Romania)
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  • Prof. Dr. Vasile I. Pârvulescu

    Corresponding author
    1. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
    • Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, B-dul Regina Elisabeta 4-13, 030016 Bucharest (Romania), Fax. (+40) 214100241
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Abstract

Postsynthetic modification of [Cu2(mand)2(hmt)] (mand=mandelic acid, hmt=hexamethylenetetramine) with a chiral, dimeric chromium(III)–salen complex led to a robust structure. Characterization of this new material showed that it perfectly preserved the textural and structural properties of the parent metal–organic framework (MOF). Although epoxidation of trans-methyl cinnamate with hydrogen peroxide led to copper leaching of 2–3 %, experiments performed with N-methylmorpholine-N-oxide indicated no leaching, even after 72 h of exposure. The obtained chiral MOF is an effective catalyst for the enantioselective epoxidation of trans-methyl cinnamate and leads to (2R,3S)-phenylglycidate with a high enantiomeric excess at room temperature.

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