Access to valuable building blocks by regio-and enantioselective ring-opening of itaconic anhydride using lipase catalysis. - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2022

Access to valuable building blocks by regio-and enantioselective ring-opening of itaconic anhydride using lipase catalysis.

Résumé

Herein, we report for the first time, the high regio- and enantioselective ring opening of a biobased itaconic anhydride catalyzed by the Pseudomonas cepacia lipase (PCL) in tert-butylmethylether (TBME) at room temperature. This approach is easy, efficient, eco-friendly and afforded in one-step a series of a highly valuable monoesters itaconates (achiral or enantioenriched) using various alcohols as nucleophiles with 100% atom economy. In all cases the β-monoester isomer was the predominant product of the reaction. Using achiral primary alcohols as substrates, a variety of novel itaconates were obtained in moderate to excellent yields (50 - 90%). For select examples, product characterization was carried out using X-ray diffraction, in addition to standard techniques. The application of this approach was performed for the preparation of enantioenriched 4-monoester itaconates via enzymatic kinetic resolution.
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Dates et versions

hal-03603787 , version 1 (10-03-2022)

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Nabila Braia, Mounia Merabet-Khelassi, Martial Toffano, Régis Guillot, Louisa Aribi-Zouioueche. Access to valuable building blocks by regio-and enantioselective ring-opening of itaconic anhydride using lipase catalysis.. Organic & Biomolecular Chemistry, 2022, ⟨10.1039/D2OB00047D⟩. ⟨hal-03603787⟩
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