Conjugate addition of amines to an alpha,beta-unsaturated imine derived from alpha-aminophosphonate. Synthesis of gamma-amino-alpha-dehydroaminophosphonates.
Aza-Michael reaction of ammonia, aliphatic, aromatic and optically active amines to an alpha,beta-unsaturated imine derived from alpha-aminophosphonate affords alpha-dehydroaminophosphonates with a gamma-stereogenic center bearing an amino group. Resulting gamma-amino alpha-dehydroaminophosphonates can be used for the preparation of phosphorylated pyrimidine derivatives.
Vicario
Javier
J
Departamento de Quimica Organica I, Facultad de Farmacia, Universidad del Pais Vasco, Apartado 450, 01080 Vitoria, Spain.
Aparicio
Domitila
D
Palacios
Francisco
F
D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D063065:Organophosphonates; D011743:Pyrimidines; C030986:pyrimidine