Department of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, Italy.
Centro Ricerche per la Chimica Fine s.r.l. for Silvateam s.p.a., Via Torre 7, 12080 San Michele Mondovì, Italy.
Molecules. 2022 Dec 5;27(23):8566. doi: 10.3390/molecules27238566.
A chiral glycerol derivative, namely 3-amino-1,2-propanediol, was employed for as the hydrogen bond donor (HBD) in the design of a new deep eutectic solvent (DES) with choline chloride acting as the hydrogen bond acceptor (HBA). The novel mixture was characterized and unambiguously classified as a DES. Furthermore, its synthetic usefulness was demonstrated in the room-temperature -butyllithium-addition under air to carbonyl compounds and benzyl chloride. In some cases, pure products (100% conversion) were obtained by a simple extractive work-up in up to 72% isolated yield, thus suggesting the potential practical usefulness of this procedure as a green alternative to the classical Schenk procedure in volatile organic solvents for the synthesis of tertiary alcohols. The chirality of the HBD, bearing an interesting basic primary amino group, is an intriguing feature currently under investigation for further exploitation.
手性甘油衍生物，即 3-氨基-1,2-丙二醇，被用作新型氢键供体（HBD）与胆碱氯化物（HBA）共同设计新型深共熔溶剂（DES）。新型混合物的特点是明确地分类为 DES。此外，它在室温下在空气中与羰基化合物和苄基氯进行丁基锂加成反应的合成具有实用性。在某些情况下，通过简单的萃取后处理，可获得纯产物（100%转化率），最高分离收率可达 72%，因此，该方法具有潜在的实际应用价值，作为传统在挥发性有机溶剂中进行的 Schenk 反应的绿色替代方法，用于合成叔醇。HBD 的手性，带有有趣的碱性伯氨基，是目前正在研究的一个有趣的特征，以进一步开发利用。
