title: Catalytic Stereodivergent Synthesis of Steroid-Fulleropyrrolidine Hybrids.
abstract: The diastereoselective synthesis of cis and trans steroid-fulleropyrrolidines hybrids by reaction of N-metalated azomethine ylides [Cu(II) or Ag(I)] with the appropriate chiral ligand and C60is described. The experimental findings reveal that the azomethine ylide stabilized by an allylic group cycloadds to [60]fullerene in an efficient manner and with a good diastereomeric excess. Furthermore, the new generated stereocenters are fully controlled by the catalytic systems used without being influenced by the chirality of the steroid. Interestingly, by this synthetic methodology the each one of the four possible stereoisomers have efficiently been obtained and characterized by CD spectra.
authors.affiliation: Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana , 10400 La Habana, Cuba.
authors.forename: Margarita
authors.initials: M
authors.lastname: Suárez
authors.affiliation: Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana , 10400 La Habana, Cuba.
authors.forename: Alberto
authors.initials: A
authors.lastname: Ruiz
authors.affiliation: Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana , 10400 La Habana, Cuba.
authors.forename: Luis
authors.initials: L
authors.lastname: Almagro
authors.affiliation: Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana , 10400 La Habana, Cuba.
authors.forename: Julieta
authors.initials: J
authors.lastname: Coro
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Enrique E
authors.initials: EE
authors.lastname: Maroto
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Salvatore
authors.initials: S
authors.lastname: Filippone
authors.affiliation: CAI RMN Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Dolores
authors.initials: D
authors.lastname: Molero
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Roberto
authors.initials: R
authors.lastname: Martínez-Álvarez
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Nazario
authors.identifier: 0000-0002-5355-1477
authors.initials: N
authors.lastname: Martín