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Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives

AutorAuria-Luna, Fernando; Marqués-López, Eugenia ; Gimeno, M. Concepción ; Heiran, Roghayeh; Mohammadi, Somayeh ; Herrera, Raquel P.
Fecha de publicación2017
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 82(11): 5516-5523 (2017)
ResumenThe first cinchona-alkaloid-organocatalyzed enantioselective synthesis of chiral 1,4-dihydropyridine derivatives is described. Bis-cinchona catalyst 3b activates the Michael addition reaction between malononitrile derivatives 2 and enamines 1, affording the appealing and highly substituted 1,4-dihydropyridines 4 with very good results in most cases. This is one of very few examples of the synthesis of chiral 1,4-dihydropyridines by an enantioselective catalytic procedure. The highly substituted final compounds are of interest for their potential biological activity. This efficient protocol opens the door to a new area of research for the asymmetric construction of these skeletons for which enantioselective syntheses are still very limited.
URIhttp://hdl.handle.net/10261/155786
DOI10.1021/acs.joc.7b00176
Identificadoresdoi: 10.1021/acs.joc.7b00176
e-issn: 1520-6904
issn: 0022-3263
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