Synthesis of alpha-phosphorylated alpha,beta-unsaturated imines and their selective reduction to vinylogous and saturated alpha-aminophosphonates.
An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.
Palacios
Francisco
F
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain. francisco.palacios@ehu.es
Vicario
Javier
J
Maliszewska
Agnieszka
A
Aparicio
Domitila
D
D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010766:Phosphorylation
D007097:Imines; D063065:Organophosphonates