Highly Efficient and Robust Enantioselective Liquid-Liquid Extraction of 1,2-Amino Alcohols utilizing VAPOL- and VANOL-based Phosphoric Acid Hosts
| Autor: | Ben L. Feringa, Johannes G. de Vries, Sander J. Wezenberg, Erik B. Pinxterhuis, Jean-Baptiste Gualtierotti |
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| Přispěvatelé: | Synthetic Organic Chemistry, Basic and Translational Research and Imaging Methodology Development in Groningen (BRIDGE) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
General Chemical Engineering
ENANTIOMERS Liquid-Liquid Extraction REACTIVE EXTRACTION CHROMATOGRAPHY BRONSTED ACID 010402 general chemistry amino alcohols 01 natural sciences host-guest systems OPTICAL RESOLUTION chemistry.chemical_compound Environmental Chemistry Organic chemistry phosphoric acids General Materials Science AMINO-ACIDS Phosphoric acid Chromatography High Pressure Liquid 010405 organic chemistry Chemistry COMPLEXATION DERIVATIVES Extraction (chemistry) Enantioselective synthesis Stereoisomerism Combinatorial chemistry Environmentally friendly Chiral resolution 0104 chemical sciences General Energy Enantiopure drug DIELS-ALDER REACTIONS extraction CHIRAL SEPARATION chiral resolution Enantiomer Brønsted–Lowry acid–base theory |
| Zdroj: | Chemsuschem, 11(1), 178-184. WILEY-V C H VERLAG GMBH |
| ISSN: | 1864-564X 1864-5631 |
| Popis: | The large-scale production of enantiopure compounds in a cost-effective and environmentally friendly manner remains one of the major challenges of modern-day chemistry. The resolution of racemates through enantioselective liquid-liquid extraction was developed as a suitable solution but has remained largely underused, owing to a lack of highly efficient and robust chiral hosts to mediate the process. This paucity of hosts can in part be attributed to a poor understanding of the underlying principles behind these processes hindering the design of more efficient selectors. A previously untested class of hosts, VAPOL and VANOL derived phosphoric acids, has been studied in depth for the efficient enantioselective liquid-liquid extraction of 1,2-amino alcohols. A systematic investigation of extraction parameters was conducted, revealing many key interactions and DFT calculations illustrate the binding modes for the 1:1 complexes that are involved in chiral recognition. The resulting, now-optimized, procedures are highly robust and easy to implement. They are also easily scalable, as demonstrated by U-tube experiments. |
| Databáze: | OpenAIRE |
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