2024-03-28T08:57:59Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1557862020-12-10T16:19:06Zcom_10261_52707com_10261_5col_10261_52708
Auria-Luna, Fernando
Marqués-López, Eugenia
Gimeno, M. Concepción
Heiran, Roghayeh
Mohammadi, Somayeh
Herrera, Raquel P.
2017-09-28T09:15:55Z
2017-09-28T09:15:55Z
2017
Journal of Organic Chemistry 82(11): 5516-5523 (2017)
http://hdl.handle.net/10261/155786
10.1021/acs.joc.7b00176
http://dx.doi.org/10.13039/501100003329
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100010067
The 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.
eng
openAccess
Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
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