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Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb "Amine"
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Number of Authors: 62019 (English)In: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 12, no 6, p. 1147-1154Article in journal (Refereed) Published
Abstract [en]

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 alpha-oxyketones and cyclic alpha-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.

Place, publisher, year, edition, pages
2019. Vol. 12, no 6, p. 1147-1154
Keywords [en]
acylation, asymmetric chemistry, chemoselectivity, green solvents, organolithium, Green & Sustainable Science & Technology
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-168367DOI: 10.1002/cssc.201802815ISI: 000461895100005PubMedID: 30614208OAI: oai:DiVA.org:su-168367DiVA, id: diva2:1314857
Available from: 2019-05-10 Created: 2019-05-10 Last updated: 2019-07-12Bibliographically approved

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Holzer, WolfgangOlofsson, BeritPace, Vittorio
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