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Issue 22, 2018
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Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol

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Abstract

A new chiral mesoporous hybrid material was synthesized based on pyrrolidine units included in a siliceous framework, HybPyr, and integrated into the organic–inorganic structure, from a specific bis-silylated precursor. A fluoride sol–gel methodology under soft synthesis conditions and in the absence of sophisticated structural directing agents allowed the generation of a mesoporous architecture with a homogeneous distribution of active chiral moieties along the network. The hybrid material was studied by means of different characterization techniques (TGA, NMR and IR spectroscopy, chemical and elemental analyses, TEM, and textural measurements), verifying the stability and integrity of the asymmetric active sites in the solid. The hybrid material, HybPyr, is an excellent asymmetric heterogeneous and recyclable catalyst for enantioselective Michael addition of linear aldehydes to β-nitrostyrene derivatives with high stereocontrol of the reaction products.

Graphical abstract: Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol

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Publication details

The article was received on 09 Aug 2018, accepted on 05 Sep 2018 and first published on 23 Oct 2018


Article type: Paper
DOI: 10.1039/C8CY01650J
Citation: Catal. Sci. Technol., 2018,8, 5835-5847
  • Open access: Creative Commons BY-NC license
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    Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol

    S. Llopis, T. García, Á. Cantín, A. Velty, U. Díaz and A. Corma, Catal. Sci. Technol., 2018, 8, 5835
    DOI: 10.1039/C8CY01650J

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