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Catalytic Stereodivergent Synthesis of Steroid–Fulleropyrrolidine Hybrids

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Suarez, Margarita and Ruiz, Alberto and Almagro, Luis and Coro, Julieta and Maroto, Enrique E. and Filippone, Salvatore and Molero, Dolores and Martínez-Alvarez, Roberto and 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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Official URL: http://pubs.acs.org/doi/full/10.1021/acs.joc.7b00286



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 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.


Item Type:Article
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:46353
Deposited On:06 Feb 2018 12:48
Last Modified:13 Apr 2018 23:01

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