title: Reaction of 2H-Azirine-Phosphine Oxides and -Phosphonates with Enolates Derived from β-Keto Esters.
abstract: Cyclopenta[b]-pyrrole-2-phosphine oxides 4a and -phosphonates 4b,c are generated by the addition of cyclic enolates derived from ethyl 2-oxo-cyclopentanecarboxylate 2 to phosphorated 2H-azirines 1. However, the addition of enolate derived from acyclic 2-oxo-butanoate 10 to 2H-azirine phosphine oxide 1 led to vinylogous N-acyl-α-aminoalkyl phosphine oxides 12, involving the carbonyl group and the Cα of the keto ester 10. Ring closure of vinylogous derivative 12 in the presence of base afforded pyrrole-2-phosphine oxide 11. The addition of enolates derived from indenone-carboxylate 15 to 2H-azirines 1 led to the formation of functionalized N-substituted 1H-benzo[d]azepine derivatives 17.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Apartado 450, 01080 Vitoria, Spain.
authors.forename: Ander
authors.initials: A
authors.lastname: Vélez Del Burgo
authors.affiliation: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Apartado 450, 01080 Vitoria, Spain.
authors.forename: Ana M
authors.initials: AM
authors.lastname: Ochoa de Retana
authors.affiliation: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Apartado 450, 01080 Vitoria, Spain.
authors.forename: Jesús M
authors.initials: JM
authors.lastname: de Los Santos
authors.affiliation: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Apartado 450, 01080 Vitoria, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Palacios