Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

Nobuhiro Takahashi; Tomoyuki Tajima; Naoki Tsugawa; Yutaka Takaguchi

doi:10.1016/j.tet.2010.07.061

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 language	English
Pages (from-to)	7787-7793
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2010.07.061
Publication status	Published - Sep 25 2010

Keywords

Diastereoselectivity
Enantiomer
Fullerene
Fullerodendron
Gluconamide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Takahashi, N., Tajima, T., Tsugawa, N., & Takaguchi, Y. (2010). Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction. Tetrahedron, 66(39), 7787-7793. https://doi.org/10.1016/j.tet.2010.07.061

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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.",

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