TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=77956385122&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77956385122&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.07.061
DO - 10.1016/j.tet.2010.07.061
M3 - Article
AN - SCOPUS:77956385122
VL - 66
SP - 7787
EP - 7793
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 39
ER -