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Título

1-Aminovinylphosphonate esters as substrates for the Diels-Alder reaction: First synthetic and theoretical study

AutorJiménez-Andreu, M. Mercedes CSIC; Bueno-Morón, Jorge; Sayago, Francisco J. CSIC ORCID; Cativiela, Carlos CSIC ORCID; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID
Palabras claveCycloaddition
Olefination
Phosphorous compounds
Density functional calculations
Strained molecules
Fecha de publicación2019
EditorWiley-VCH
CitaciónEuropean Journal of Organic Chemistry (6): 1268-1272 (2019)
ResumenThe Diels‐Alder reaction of 1‐aminovinylphosphonate esters has been studied for the first time as a suitable procedure leading to quaternary carbocyclic α‐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.
Versión del editorhttps://doi.org/10.1002/ejoc.201801633
URIhttp://hdl.handle.net/10261/187172
DOI10.1002/ejoc.201801633
ISSN1434-193X
E-ISSN1099-0690
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