Michael addition of amine derivatives to conjugate phosphinyl and phosphonyl nitrosoalkenes. Preparation of alpha-amino phosphine oxide and phosphonate derivatives.
The synthesis of nitrosoalkenes derived from phosphine oxides and phosphonates generated through base-mediated dehydrohalogenations of readily available alpha-halooximes is reported. These highly reactive intermediates act as Michael acceptors toward nucleophilic reagents such as ammonia, amines, and optically active amino esters, furnishing alpha-amino phosphine oxides and phosphonates in a highly regioselective fashion.
de los Santos
Jesús M
JM
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain.
Ignacio
Roberto
R
Aparicio
Domitila
D
Palacios
Francisco
F
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000641:Ammonia / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D010766:Phosphorylation
D000475:Alkenes; D000588:Amines; D001372:Aza Compounds; D004952:Esters; D006219:Halogens; D063065:Organophosphonates; D010087:Oxides; D010091:Oximes; D010720:Phosphines; D000641:Ammonia; D006859:Hydrogen; C044646:phosphine; D009584:Nitrogen