Reaction of 2H-azirine phosphine oxide and -phosphonates with nucleophiles. Stereoselective Synthesis of functionalized aziridines and alpha- and beta-aminophosphorus derivatives.
[reaction: see text] A simple and efficient stereoselective synthesis of aziridine-2-phosphonate 3, and -phosphine oxide 5 by diastereoselective addition of Grignard reagents to 2H-azirine phosphonate 1 and -phosphine oxide 4 is reported. Similarly, the addition of heterocyclic amines and benzenethiol to aziridines 1 and 4 yielded functionalized aziridines 10, 11, and 18. These aziridines are used as intermediates for the regioselective synthesis of beta-aminophosphine oxides 6 and beta-aminophosphonates 7, as well as alpha- aminophosphonates 8. Phenylsulfenyl-substituted alpha-aminophosphorus derivatives 15 and 19 are obtained directly from benzenethiol and 2H-azirine phosphonates 1 and -phosphine oxides 4.
Palacios
Francisco
F
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Vitoria, Spain. francisco.palacios@ehu.cs
de Retana
Ana M Ochoa
AM
Alonso
José M
JM
D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry
C510918:2H-azirine phosphine oxide; D001388:Aziridines; D007093:Imidazoles; D063065:Organophosphonates; D010720:Phosphines; D010797:Phthalimides; C037431:phthalimide; D013455:Sulfur; C029899:imidazole; C044646:phosphine