Levoglucosenone as a starting material for cascade continuous-flow synthesis of (R)-γ-carboxy-γ-butyrolactone.

Autor:	Pacheco CM; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., Lima W; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., Lima FA; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., Gomez MRBP; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., da Silva IG; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., Miranda LSM; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., Esteves PM; Instituto de Química, Universidade Federal do Rio de Janeiro Av. Athos da Silveira Ramos, 149, CT, A-622, Cid. Univ. Rio de Janeiro RJ 21941-909 Brazil., Itabaiana I Jr; Department of Biochemical Engineering, School of Chemistry, Federal University of Rio de Janeiro Rio de Janeiro 21941909 Brazil., Wojcieszak R; Univ. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181 - UCCS - Unité de Catalyse et Chimie du Solide Lille France.; Université de Lorraine, CNRS, L2CM UMR 7053 Nancy F-54000 France souzarod21@gmail.com., Leão RAC; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil., de Souza ROMA; Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil.
Jazyk:	angličtina
Zdroj:	RSC advances [RSC Adv] 2024 Oct 29; Vol. 14 (47), pp. 34611-34619. Date of Electronic Publication: 2024 Oct 29 (Print Publication: 2024).
DOI:	10.1039/d4ra06403h
Abstrakt:	The global imperative to shift towards renewable and sustainable resources has spurred significant interest in exploring and utilizing platform chemicals derived from renewable feedstocks. Among these, levoglucosenone (LGO) and Cyrene™ have emerged as promising candidates. LGO, derived from the pyrolysis of cellulose and hemicellulose, exhibits structural versatility, making it an attractive starting material for various valuable products. Its chemical transformations can yield a diverse array of derivatives, including levulinic acid, furan derivatives, and intermediates for pharmaceutical and agrochemical synthesis, as well as bio-based materials such as bioplastics and resins. Cyrene™, produced through the hydrogenation of LGO, serves as a renewable, biodegradable, and non-toxic dipolar aprotic solvent, offering sustainability advantages for green chemistry applications. Herein we report our results on the continuous-flow cascade transformation of LGO into Cyrene™ and then (R)-γ-carboxy-γ-butyrolactone in good yields with an additional mechanistic investigation for the Baeyer-Villiger oxidation of Cyrene™. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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