Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization
SERGEY SERGEYEV
1
,
MO Schär
1
,
Paul Seiler
1
,
Olena Lukoyanova
2
,
Luis Echegoyen
2
,
Francois Diederich
1
Publication type: Journal Article
Publication date: 2005-01-26
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
15674978
General Chemistry
Catalysis
Organic Chemistry
Abstract
The double Bingel reaction of fullerene C60 with bismalonates attached to a Tröger base derived tether afforded trans-1, trans-2, trans-3, and trans-4 bisadducts with excellent regioselectivity. In particular, enantiomerically pure bisadducts with inherently chiral trans-2 or trans-3 addition patterns were prepared starting from enantiomerically pure bismalonates. The absolute configuration of the trans-2 and trans-3 bisadducts was established from their CD spectra. The excellent diastereoselectivity in the double additions to give the trans-2 bisadducts is particularly remarkable given the large distance between the two reacting bonds in opposite hemispheres of the fullerene that is spanned by the tether. Now, all inherently chiral double addition patterns are readily available by tether-directed functionalization using appropriate chiral, nonracemic spacers.
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70
Total citations:
70
Citations from 2025:
2
(2.86%)
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SERGEYEV S. et al. Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization // Chemistry - A European Journal. 2005. Vol. 11. No. 8. pp. 2284-2294.
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SERGEYEV S., Schär M., Seiler P., Lukoyanova O., Echegoyen L., Diederich F. Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization // Chemistry - A European Journal. 2005. Vol. 11. No. 8. pp. 2284-2294.
Cite this
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TY - JOUR
DO - 10.1002/chem.200401253
UR - https://doi.org/10.1002/chem.200401253
TI - Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization
T2 - Chemistry - A European Journal
AU - SERGEYEV, SERGEY
AU - Schär, MO
AU - Seiler, Paul
AU - Lukoyanova, Olena
AU - Echegoyen, Luis
AU - Diederich, Francois
PY - 2005
DA - 2005/01/26
PB - Wiley
SP - 2284-2294
IS - 8
VL - 11
PMID - 15674978
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2005_SERGEYEV,
author = {SERGEY SERGEYEV and MO Schär and Paul Seiler and Olena Lukoyanova and Luis Echegoyen and Francois Diederich},
title = {Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization},
journal = {Chemistry - A European Journal},
year = {2005},
volume = {11},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/chem.200401253},
number = {8},
pages = {2284--2294},
doi = {10.1002/chem.200401253}
}
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SERGEYEV, SERGEY, et al. “Synthesis oftrans-1,trans-2,trans-3, andtrans-4 Bisadducts of C60by Regio- and Stereoselective Tether-Directed Remote Functionalization.” Chemistry - A European Journal, vol. 11, no. 8, Jan. 2005, pp. 2284-2294. https://doi.org/10.1002/chem.200401253.