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Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine and Weinreb "Amine".

著者 Monticelli S , Holzer W , Langer T , Roller A , Olofsson B , Pace V
ChemSusChem.2019 Jan 07 ; ():.
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The well-established Hoppe-Beak chemistry, which involves enantioselective generation of organolithiums in the presence of (-)-sparteine, has been 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.
PMID: 30614208 [PubMed - as supplied by publisher]
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