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Molecules


Title:"Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry"
Author(s):Antenucci A; Bonomo M; Ghinato S; Blangetti M; Dughera S;
Address:"Department of Chemistry, Universita 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 Mondovi, Italy. NIS Interdepartmental Centre and INSTM Reference Centre, Universita degli Studi di Torino, Via Gioacchino Quarello 15/a, 10125 Torino, Italy"
Journal Title:Molecules
Year:2022
Volume:20221205
Issue:23
Page Number: -
DOI: 10.3390/molecules27238566
ISSN/ISBN:1420-3049 (Electronic) 1420-3049 (Linking)
Abstract:"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 n-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"
Keywords:"*Deep Eutectic Solvents *Propylene Glycol Solvents/chemistry Choline/chemistry 3-amino-1, 2-propanediol deep eutectic solvent organolithium reagents;"
Notes:"MedlineAntenucci, Achille Bonomo, Matteo Ghinato, Simone Blangetti, Marco Dughera, Stefano eng Switzerland 2022/12/12 Molecules. 2022 Dec 5; 27(23):8566. doi: 10.3390/molecules27238566"

 
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