Access to valuable building blocks by the regio- and enantioselective ring opening of itaconic anhydride by lipase catalysis.
Org Biomol Chem
; 20(13): 2693-2703, 2022 03 30.
Article
em En
| MEDLINE
| ID: mdl-35293925
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 ß-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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Lipase
/
Anidridos
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article