Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, Russia.
Laboratory of Functional Composite Materials, Bauman Moscow State Technical University, 2nd Baumanskaya Street 5/1, 105005 Moscow, Russia.
Int J Mol Sci. 2021 Nov 1;22(21):11856. doi: 10.3390/ijms222111856.
A recent strong trend toward green and sustainable chemistry has promoted the intensive use of renewable carbon sources for the production of polymers, biofuels, chemicals, monomers and other valuable products. The Diels-Alder reaction is of great importance in the chemistry of renewable resources and provides an atom-economic pathway for fine chemical synthesis and for the production of materials. The biobased furans furfural and 5-(hydroxymethyl)furfural, which can be easily obtained from the carbohydrate part of plant biomass, were recognized as "platform chemicals" that will help to replace the existing oil-based refining to biorefining. Diels-Alder cycloaddition of furanic dienes with various dienophiles represents the ideal example of a "green" process characterized by a 100% atom economy and a reasonable E-factor. In this review, we first summarize the literature data on the regio- and diastereoselectivity of intermolecular Diels-Alder reactions of furfural derivatives with alkenes with the aim of establishing the current progress in the efficient production of practically important low-molecular-weight products. The information provided here will be useful and relevant to scientists in many fields, including medical and pharmaceutical research, polymer development and materials science.
近期绿色可持续化学的发展趋势推动了可再生碳源在聚合物、生物燃料、化学品、单体和其他有价值产品生产中的集约化利用。Diels-Alder 反应在可再生资源化学中具有重要意义，为精细化学品合成和材料生产提供了一种原子经济性途径。生物基呋喃糠醛和 5-羟甲基糠醛可以很容易地从植物生物质的碳水化合物部分获得，它们被认为是“平台化学品”，有助于取代现有的基于石油的精炼工艺向生物炼制工艺的转变。呋喃二烯与各种亲双烯体的 Diels-Alder 环加成反应是“绿色”过程的理想示例，其具有 100%的原子经济性和合理的 E 因子。在这篇综述中，我们首先总结了文献中关于糠醛衍生物与烯烃的分子间 Diels-Alder 反应的区域和立体选择性的数据，旨在确定高效生产实用的低分子量产品的最新进展。这里提供的信息将对包括医学和药物研究、聚合物开发和材料科学在内的许多领域的科学家有用且相关。
