Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb 'Amine'
| Autor: | Alexander Roller, Thierry Langer, Serena Monticelli, Wolfgang Holzer, Vittorio Pace, Berit Olofsson |
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| Rok vydání: | 2018 |
| Předmět: |
General Chemical Engineering
asymmetric chemistry Cyclopentyl methyl ether 02 engineering and technology 010402 general chemistry 01 natural sciences Acylation chemistry.chemical_compound medicine acylation Environmental Chemistry Organic chemistry General Materials Science Chemoselectivity Derivatization Green & Sustainable Science & Technology green solvents Full Paper Chemistry organolithium Sparteine Enantioselective synthesis Kemi Full Papers 021001 nanoscience & nanotechnology 0104 chemical sciences Solvent General Energy chemoselectivity Chemical Sciences Amine gas treating 0210 nano-technology medicine.drug |
| Zdroj: | Chemsuschem |
| ISSN: | 1864-564X |
| Popis: | The well‐established Hoppe–Beak chemistry, which involves enantioselective generation of organolithium compounds in the presence of (−)‐sparteine, was revisited and applied to unprecedented acylations with Weinreb amides to access highly enantioenriched α‐oxyketones and cyclic α‐aminoketones. Recycling of the sustainable solvent cyclopentyl methyl ether, sparteine, and the released Weinreb “amine” [HNMe(OMe)] was possible through a simple work‐up procedure that enabled full recovery of these precious materials. The methodology features a robust scope and flexibility, thus allowing the enantioselective preparation of scaffolds amenable of further derivatization. |
| Databáze: | OpenAIRE |
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