Diastereoselective lithium salt-assisted 1,3-dipolar cycloaddition of azomethine ylides to the fullerene C60

Vitaliy A. Ioutsi, Alexander A. Zadorin, Pavel A. Khavrel, Nikita M. Belov, Natalia S. Ovchinnikova, Alexey A. Goryunkov, Oleg N. Kharybin, Eugenii N. Nikolaev, Marina A. Yurovskaya, Lev N. Sidorov

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

An efficient method for the diastereoselective synthesis of 5-substituted 3,4-fulleroproline esters based on the lithium salt-assisted cycloaddition of azomethine ylides has been developed. A series of the fulleroproline esters containing either electron donating or electron withdrawing substituents was prepared with high yields and diastereoselectivities provided by the S-trans-configuration of ylide generated in situ from the corresponding Schiff base in the presence of a lithium salt and base. This method provides easy preparation of 3,4-fulleroproline derivatives suitable for fullerene-based peptide synthesis.

Original languageEnglish
Pages (from-to)3037-3041
Number of pages5
JournalTetrahedron
Volume66
Issue number16
DOIs
Publication statusPublished - 17 Apr 2010
Externally publishedYes

Keywords

  • Azomethine ylide
  • Diastereoselectivity
  • Fulleroproline
  • Lithium salt-assisted 1,3-dipolar cycloaddition

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