Access to valuable building blocks by the regio- and enantioselective ring opening of itaconic anhydride by lipase catalysis. Issue 13 (16th March 2022)

• Record Type: Journal Article
• Authors: Braïa, Nabila; Merabet-Khelassi, Mounia; Toffano, Martial; Guillot, Regis; Aribi-Zouioueche, Louisa
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 13(2022)
• Page Start: 2693
• Page End: 2703
• Publication Date: 2022-03-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00047d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Herein, we report for the first time the highly regio- and enantioselective ring opening of a biobased itaconic anhydride catalyzed by the Pseudomonas cepacia lipase ( PCL ) in tert -butyl methyl ether (TBME) at room temperature. Abstract : Herein, we report for the first time the highly regio- and enantioselective ring opening of a biobased itaconic anhydride catalyzed by the Pseudomonas cepacia lipase ( PCL ) in tert -butyl methyl ether (TBME) at room temperature. This method is easy, efficient and eco-friendly and can be performed in one step with a series of highly valuable monoester 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 the standard techniques. The application of this approach was performed for the preparation of enantioenriched 4-monoester itaconates via enzymatic kinetic resolution.