Regioselective synthesis of fluoroalkylated beta-aminophosphorus derivatives and aziridines from phosphorylated oximes and nucleophilic reagents.
A simple and efficient stereoselective synthesis of fluoroalkyl substituted aziridine-2-phosphine oxides and -phosphonates by diastereoselective addition of methoxide, imidazole, benzenethiol, and Grignard reagents to functionalized ketoxime-phosphine oxides and -phosphonates is described. Aziridines are used as intermediates for the regioselective synthesis of fluorine containing beta-amino phosphine oxides and beta-amino phosphonates. Amino phosphorus derivatives can also be obtained from ketoximes derived from phosphine oxides and phosphonates with sodium borohydride.
Palacios
Francisco
F
Departamento de Química Organica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080, Vitoria, Spain. francisco.palacios@ehu.es
Ochoa de Retana
Ana M
AM
Alonso
José M
JM
D000478:Alkylation; D000586:Amination; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D010766:Phosphorylation; D013237:Stereoisomerism
D001388:Aziridines; D007659:Ketones; D010091:Oximes; D010758:Phosphorus; D005461:Fluorine; C033132:aziridine