First aromatic amine organocatalysed activation of alpha, beta- unsaturated ketones

Sonsona, I.G. ; Marques-Lopez, E. (Universidad de Zaragoza) ; Gimeno, M.C. (Universidad de Zaragoza) ; Herrera, R.P.

Resumen: This work provides an unprecedented example of a chiral aromatic amine used to activate a, b-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a-f) and coumarins (2a-d). The reaction gives rise to warfarin derivatives 3 with promising results using this family of catalysts for the first time. The additional studies performed supported the bifunctional mode of activation of the chiral catalyst VII and the covalent nature of the interactions between the catalyst VII and benzylideneacetones 1.

Idioma: Inglés

DOI: 10.1039/c9nj02392e

Año: 2019

Publicado en: NEW JOURNAL OF CHEMISTRY 43, 31 (2019), 12233-12240
ISSN: 1144-0546

Factor impacto JCR: 3.288 (2019)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 68 / 177 = 0.384 (2019) - Q2 - T2

Factor impacto SCIMAGO: 0.712 - Materials Chemistry (Q1) - Chemistry (miscellaneous) (Q2) - Catalysis (Q3)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-75816-C2-1-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2017-88091-P
Financiación: info:eu-repo/grantAgreement/ES/UZ/JIUZ-2017-CIE-05

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)