Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

Nobuhiro Takahashi, Tomoyuki Tajima, Naoki Tsugawa, Yutaka Takaguchi

Research output: Contribution to journal › Article

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

Fingerprint

Fullerenes
Spectroscopic analysis
Cycloaddition
Cycloaddition Reaction
Nuclear magnetic resonance spectroscopy
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Magnetic Resonance Spectroscopy
dendron
gluconamide
Carbon-13 Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy

Keywords

  • Diastereoselectivity
  • Enantiomer
  • Fullerene
  • Fullerodendron
  • Gluconamide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction. / Takahashi, Nobuhiro; Tajima, Tomoyuki; Tsugawa, Naoki; Takaguchi, Yutaka.

In: Tetrahedron, Vol. 66, No. 39, 25.09.2010, p. 7787-7793.

Research output: Contribution to journal › Article

Takahashi, N, Tajima, T, Tsugawa, N & Takaguchi, Y 2010, 'Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction', Tetrahedron, vol. 66, no. 39, pp. 7787-7793. https://doi.org/10.1016/j.tet.2010.07.061
Takahashi N, Tajima T, Tsugawa N, Takaguchi Y. Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction. Tetrahedron. 2010 Sep 25;66(39):7787-7793. https://doi.org/10.1016/j.tet.2010.07.061
Takahashi, Nobuhiro ; Tajima, Tomoyuki ; Tsugawa, Naoki ; Takaguchi, Yutaka. / Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction. In: Tetrahedron. 2010 ; Vol. 66, No. 39. pp. 7787-7793.
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