1236884-64-2Relevant academic research and scientific papers
1-Aminovinylphosphonate Esters as Substrates for the Diels-Alder Reaction: First Synthetic and Theoretical Study
Jiménez-Andreu, M. Mercedes,Bueno-Morón, Jorge,Sayago, Francisco J.,Cativiela, Carlos,Tejero, Tomás,Merino, Pedro
, p. 1268 - 1272 (2019)
The 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.
