Pacheco Caio M, Lima Wesley, Lima Fernanda A, Gomez Mauro R B P, da Silva Isabela G, Miranda Leandro S M, Esteves Pierre M, Itabaiana Ivaldo, Wojcieszak Robert, Leão Raquel A C, de Souza Rodrigo O M A
Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro Rio de Janeiro 21941910 Brazil.
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.
RSC Adv. 2024 Oct 29;14(47):34611-34619. doi: 10.1039/d4ra06403h.
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™.
向可再生和可持续资源转型的全球迫切需求激发了人们对探索和利用源自可再生原料的平台化学品的浓厚兴趣。其中，左旋葡萄糖酮（LGO）和Cyrene™已成为有前景的候选物。LGO由纤维素和半纤维素热解产生，具有结构多样性，使其成为各种有价值产品的有吸引力的起始原料。其化学转化可产生多种衍生物，包括乙酰丙酸、呋喃衍生物以及用于药物和农用化学品合成的中间体，还有生物基材料，如生物塑料和树脂。通过LGO氢化生产的Cyrene™用作可再生、可生物降解且无毒的偶极非质子溶剂，为绿色化学应用提供了可持续性优势。在此，我们报告了将LGO连续流级联转化为Cyrene™，然后再转化为（R）-γ-羧基-γ-丁内酯的良好产率结果，并对Cyrene™的拜耳-维利格氧化进行了额外的机理研究。
