Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

Nobuhiro Takahashi, Tomoyuki Tajima, Naoki Tsugawa, Yutaka Takaguchi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The Diels-Alder reaction between C60 and anthryl glycodendron, which has d- or l-gluconamides at the terminals, gave a new fullerene glycodendron conjugate. Interestingly, the diastereoselective cycloaddition reaction proceeded upon the treatment of C60 with the anthryl dendron 3. Furthermore, optical pure fullerodendrons (-)-4L and (+)-4D, which were confirmed by 1H and 13C NMR spectroscopy, FT-IR, MALDI-TOF mass spectroscopic analysis, were isolated from the mixture of diastereomers. And their absolute configurations were predicted by the use of CD spectra.

Original languageEnglish
Pages (from-to)7787-7793
Number of pages7
JournalTetrahedron
Volume66
Issue number39
DOIs
Publication statusPublished - Sep 25 2010

Keywords

  • Diastereoselectivity
  • Enantiomer
  • Fullerene
  • Fullerodendron
  • Gluconamide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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