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Non-covalent interactions in the diastereoselective synthesis of cis-2,3-dihydrobenzofurans: experimental and computational studies.
Jamis-Oliva, Omar; López, Roger; Galdámez, Antonio; Gallardo-Fuentes, Sebastián; Vilches-Herrera, Marcelo.
Afiliación
  • Jamis-Oliva O; Faculty of Sciences, University of Chile, Department of Chemistry, Las Palmeras 3425, Ñuñoa, 7750000, Santiago, Chile. luis.vilches@u.uchile.cl.
  • López R; Faculty of Sciences, University of Chile, Department of Chemistry, Las Palmeras 3425, Ñuñoa, 7750000, Santiago, Chile. luis.vilches@u.uchile.cl.
  • Galdámez A; Faculty of Sciences, University of Chile, Department of Chemistry, Las Palmeras 3425, Ñuñoa, 7750000, Santiago, Chile. luis.vilches@u.uchile.cl.
  • Gallardo-Fuentes S; Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Avenida Universidad 330, Curauma, 2373223, Valparaíso, Chile.
  • Vilches-Herrera M; Faculty of Sciences, University of Chile, Department of Chemistry, Las Palmeras 3425, Ñuñoa, 7750000, Santiago, Chile. luis.vilches@u.uchile.cl.
Org Biomol Chem ; 22(7): 1441-1446, 2024 Feb 14.
Article en En | MEDLINE | ID: mdl-38265299
ABSTRACT
The diastereoselective synthesis of 2,3-DHBs has been previously reported via an intramolecular Michael addition reaction using alkali bases such as Cs2CO3 and K2CO3. However, no systematic study has been performed to understand the possible role of bases in the mechanism of the reaction and factors behind the stereoselective outcome of the reaction. Herein, from experimental and theoretical points of view, we disclose the role of the cesium salt in the rate-determining step along the catalytic cycle and the key role of stabilizing non-covalent interactions in the stereoselective outcome of the reaction.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Chile Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Chile Pais de publicación: Reino Unido