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Abstract:

A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic steps of this new reaction. Extended studies revealed that β-alkyl-substituted α,β-unsaturated aldehydes and aliphatic lithium reagents did not afford good yields of the tandem reaction products, while aromatic lithium reagents gave good results. The aggregation features of the aryllithium reagents and the extended charged delocalization effects are considered to promote β-selectivity. This approach provides a convenient route for the synthesis of a wide variety of β-alkyl-substituted dihydrochalcones.

Registro:

Documento: Artículo
Título:Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes
Autor:Nudelman, N.S.; García, G.V.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:aldehyde derivative; chalcone derivative; cinnamaldehyde; dihydrochalcone; lithium derivative; phenyllithium; unclassified drug; alkylation; article; chemical structure; nuclear magnetic resonance spectroscopy; reaction analysis; synthesis
Año:2001
Volumen:66
Número:4
Página de inicio:1387
Página de fin:1394
DOI: http://dx.doi.org/10.1021/jo005698d
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:cinnamaldehyde, 104-55-2; dihydrochalcone, 1083-30-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v66_n4_p1387_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S. & García, G.V. (2001) . Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes. Journal of Organic Chemistry, 66(4), 1387-1394.
http://dx.doi.org/10.1021/jo005698d
---------- CHICAGO ----------
Nudelman, N.S., García, G.V. "Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes" . Journal of Organic Chemistry 66, no. 4 (2001) : 1387-1394.
http://dx.doi.org/10.1021/jo005698d
---------- MLA ----------
Nudelman, N.S., García, G.V. "Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes" . Journal of Organic Chemistry, vol. 66, no. 4, 2001, pp. 1387-1394.
http://dx.doi.org/10.1021/jo005698d
---------- VANCOUVER ----------
Nudelman, N.S., García, G.V. Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes. J. Org. Chem. 2001;66(4):1387-1394.
http://dx.doi.org/10.1021/jo005698d