Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids

Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids
Julieta Coro, Margarita Suárez, Alberto Ruiz, Luis Almagro, Dolores Molero, Roberto Martínez-Álvarez, Salvatore Filippone, Enrique E. Maroto, Nazario Martín
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00286

DOI: 10.1021/acs.joc.7b00286

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