期刊
CHEMSUSCHEM
卷 12, 期 6, 页码 1147-1154出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201802815
关键词
acylation; asymmetric chemistry; chemoselectivity; green solvents; organolithium
资金
- University of Vienna
- Stockholm University
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.
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