Leonardi Gabriella, Bertuzzi Aurora, Truscello Ada, Gambarotti Cristian, Sebastiano Roberto
Department of Chemistry, Materials and Chemical Engineering "Giulio Natta", Politecnico di Milano, piazza Leonardo da Vinci 32, Milano I-20133, Italy.
ACS Omega. 2025 Jul 7;10(28):30660-30669. doi: 10.1021/acsomega.5c02695. eCollection 2025 Jul 22.
3-Hydroxy-2-pyrone-6-carboxylic acid is a versatile chemical easily prepared from aldaric acids, a family of compounds obtained from renewable resources. Herein, an efficient synthesis of dihydroxyadipic acid by catalytic hydrogenation of this pyrone at room temperature and atmospheric pressure is reported. The reaction performed in organic solvents showed high diastereoselectivity, resulting in the possibility to obtain the racemic mixture of dihydroxyadipic acid (R,R) and (S,S) that was further converted to the dilactone 2,5-dioxabicyclo[2.2.2]-octane-3,6-dione by a double intramolecular condensation reaction. This compound is a promising comonomer and/or chain-extender in the synthesis of polymers. As an example, a preliminary test of the polymerization reaction of the dilactone in the presence of a diamine is reported.
3-羟基-2-吡喃酮-6-羧酸是一种用途广泛的化学品，可轻松由醛糖二酸制备而成，醛糖二酸是一类从可再生资源中获取的化合物。本文报道了在室温和大气压下通过该吡喃酮的催化氢化高效合成二羟基己二酸的方法。在有机溶剂中进行的反应显示出高非对映选择性，从而有可能获得二羟基己二酸（R,R）和（S,S）的外消旋混合物，该混合物通过双分子内缩合反应进一步转化为双内酯2,5-二氧杂双环[2.2.2]辛烷-3,6-二酮。该化合物是聚合物合成中有前景的共聚单体和/或扩链剂。例如，报道了在二胺存在下双内酯聚合反应的初步测试。
