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 › peer-review

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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10.1016/j.tet.2010.07.061

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title = "Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction",

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.",

keywords = "Diastereoselectivity, Enantiomer, Fullerene, Fullerodendron, Gluconamide",

author = "Nobuhiro Takahashi and Tomoyuki Tajima and Naoki Tsugawa and Yutaka Takaguchi",

note = "Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (No. 21510103, 21750043 ) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) , Japan, and Support Unit for Strategic Programs at Okayama University funded by the MEXT. ",

year = "2010",

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doi = "10.1016/j.tet.2010.07.061",

language = "English",

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T1 - Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

AU - Takahashi, Nobuhiro

AU - Tajima, Tomoyuki

AU - Tsugawa, Naoki

AU - Takaguchi, Yutaka

N1 - Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (No. 21510103, 21750043 ) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) , Japan, and Support Unit for Strategic Programs at Okayama University funded by the MEXT.

PY - 2010/9/25

Y1 - 2010/9/25

N2 - 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.

AB - 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.

KW - Diastereoselectivity

KW - Enantiomer

KW - Fullerene

KW - Fullerodendron

KW - Gluconamide

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JF - Tetrahedron

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ER -

Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

Abstract

Keywords

ASJC Scopus subject areas

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