title: Asymmetric synthesis of 2H-azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids.
abstract: A simple and efficient asymmetric synthesis of 2H-azirine-2-phosphine oxides 3 is described. The key step is a solid-phase bound achiral or chiral amine-mediated Neber reaction of beta-ketoxime tosylates derived from phosphine oxides 1. Reaction of 2H-azirines 3 and 11 with carboxylic acids 4 gives phosphorylated ketamides 5 and 12. Ring closure of ketamides 5 and 12 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of phosphorylated oxazoles 8 and 13.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain. qoppagaf@vf.ehu.es
authors.forename: Francisco
authors.initials: F
authors.lastname: Palacios
authors.forename: Domitila
authors.initials: D
authors.lastname: Aparicio
authors.forename: Ana María
authors.initials: AM
authors.lastname: Ochoa De Retana
authors.forename: Jesús M
authors.initials: JM
authors.lastname: de los Santos
authors.forename: José Ignacio
authors.initials: JI
authors.lastname: Gil
authors.forename: José María
authors.initials: JM
authors.lastname: Alonso
mesh_terms: D000588:Amines / Q000737:chemistry*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D007202:Indicators and Reagents; D010720:Phosphines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D001389:Azirines; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D010720:Phosphines