108183-41-1Relevant articles and documents
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 (2019/01/24)
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.
Synthese von 1-Aminophosphonsaeure ueber Acyliminophosphonsaeure-Ester
Schrader, Thomas,Kober, Reiner,Steglich, Wolfgang
, p. 372 - 375 (2007/10/02)
1-Acylaminomethylphosphonates 1 on reaction with N-bromosuccinimide yield 1-acylamino-1-bromomethylphosphonates 2, which on treatment with tertiary amines are converted into acyliminophosphonates 3.The latter react in situ with nucleophiles like enamines,