Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry
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 D...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/23/8566 |
| _version_ | 1827642832027910144 |
|---|---|
| author | Achille Antenucci Matteo Bonomo Simone Ghinato Marco Blangetti Stefano Dughera |
| author_facet | Achille Antenucci Matteo Bonomo Simone Ghinato Marco Blangetti Stefano Dughera |
| author_sort | Achille Antenucci |
| collection | DOAJ |
| description | 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 <i>n</i>-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. |
| first_indexed | 2024-03-09T17:38:30Z |
| format | Article |
| id | doaj.art-33423f33668f4778a35acdbaed71dc9d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:38:30Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-33423f33668f4778a35acdbaed71dc9d2023-11-24T11:44:36ZengMDPI AGMolecules1420-30492022-12-012723856610.3390/molecules27238566Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium ChemistryAchille Antenucci0Matteo Bonomo1Simone Ghinato2Marco Blangetti3Stefano Dughera4Department of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, ItalyDepartment of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, ItalyDepartment of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, ItalyDepartment of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, ItalyDepartment of Chemistry, Università degli Studi di Torino, Via Pietro Giuria 7, 10125 Torino, ItalyA 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 <i>n</i>-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.https://www.mdpi.com/1420-3049/27/23/8566deep eutectic solventorganolithium reagents3-amino-1,2-propanediol |
| spellingShingle | Achille Antenucci Matteo Bonomo Simone Ghinato Marco Blangetti Stefano Dughera Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry Molecules deep eutectic solvent organolithium reagents 3-amino-1,2-propanediol |
| title | Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry |
| title_full | Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry |
| title_fullStr | Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry |
| title_full_unstemmed | Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry |
| title_short | Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry |
| title_sort | design of a new chiral deep eutectic solvent based on 3 amino 1 2 propanediol and its application in organolithium chemistry |
| topic | deep eutectic solvent organolithium reagents 3-amino-1,2-propanediol |
| url | https://www.mdpi.com/1420-3049/27/23/8566 |
| work_keys_str_mv | AT achilleantenucci designofanewchiraldeepeutecticsolventbasedon3amino12propanediolanditsapplicationinorganolithiumchemistry AT matteobonomo designofanewchiraldeepeutecticsolventbasedon3amino12propanediolanditsapplicationinorganolithiumchemistry AT simoneghinato designofanewchiraldeepeutecticsolventbasedon3amino12propanediolanditsapplicationinorganolithiumchemistry AT marcoblangetti designofanewchiraldeepeutecticsolventbasedon3amino12propanediolanditsapplicationinorganolithiumchemistry AT stefanodughera designofanewchiraldeepeutecticsolventbasedon3amino12propanediolanditsapplicationinorganolithiumchemistry |