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Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids

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Suarez, Margarita y Ruiz, Alberto y Almagro, Luis y Coro, Julieta y Maroto, Enrique E. y Filippone, Salvatore y Molero, Dolores y Martínez-Alvarez, Roberto y Martín León, Nazario (2017) Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids. Journal of organic chemistry, 82 (9). pp. 4654-4660. ISSN 0022-3263 (Print) 1520-6904 (On line))

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URL Oficial: http://pubs.acs.org/doi/full/10.1021/acs.joc.7b00286



Resumen

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 C60 is 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.


Tipo de documento:Artículo
Materias:Ciencias > Química > Química orgánica
Código ID:46353
Depositado:06 Feb 2018 12:48
Última Modificación:13 Abr 2018 23:01

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