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- Title
1‐Aminovinylphosphonate Esters as Substrates for the Diels‐Alder Reaction: First Synthetic and Theoretical Study.
- Authors
Jiménez‐Andreu, M. Mercedes; Bueno‐Morón, Jorge; Sayago, Francisco J.; Cativiela, Carlos; Tejero, Tomás; Merino, Pedro
- Abstract
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. 1‐Aminovinylphosphonate esters have been studied as Diels‐Alder reaction substrates for the first time. The influence on the course of the reaction of substituents and protecting groups on the phosphonate and amine functions has been considered and rationalized by DFT methods.
- Subjects
DIELS-Alder reaction; CARBOCYCLIC acids; AMINO group; PHOSPHONATES; DENSITY functional theory
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 6, p1268
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801633