1-Aminovinylphosphonate Esters as Substrates for the Diels-Alder Reaction: First Synthetic and Theoretical Study

Jiménez-Andreu, M.M. ; Bueno-Morón, J. ; Sayago, F.J. (Universidad de Zaragoza) ; Cativiela, C. (Universidad de Zaragoza) ; Tejero, T. (Universidad de Zaragoza) ; Merino, P. (Universidad de Zaragoza)

Resumen: The Diels-Alder reaction of 1-aminovinylphosphonate esters has been studied for the first time as a suitable procedure leading to quaternary carbocyclic a-aminophosphonates. The reaction is influenced by steric effects at the phosphonate functionality (bulky groups hinder the reaction) and electronic effects at the amino group (electron-withdrawing substituents increase the reaction rate). The exo/endo ratio is constant, and no influence of the solvent is observed. The experimental results have been rationalized by DFT methods.

Idioma: Inglés

DOI: 10.1002/ejoc.201801633

Año: 2019

Publicado en: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2019, 6 (2019), 1268–1272
ISSN: 1434-193X

Factor impacto JCR: 2.889 (2019)

Categ. JCR: CHEMISTRY, ORGANIC rank: 19 / 57 = 0.333 (2019) - Q2 - T2

Factor impacto SCIMAGO: 0.863 - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E19-17R
Financiación: info:eu-repo/grantAgreement/ES/DGA/E34-R17
Financiación: info:eu-repo/grantAgreement/ES/DGA/FSE
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2013-40855-R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2016-76155-R

Tipo y forma: Article (PostPrint)

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