TY - JOUR
T1 - Synthesis of trans-1, trans-2, trans-3, and trans-4 bisadducts of C 60 by regio-and stereoselective tether-directed remote functionalization
AU - Sergeyev, Sergey
AU - Schär, Michael
AU - Seiler, Paul
AU - Lukoyanova, Olena
AU - Echegoyen, Luis
AU - Diederich, François
PY - 2005/4/8
Y1 - 2005/4/8
N2 - 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, non-racemic spacers.
AB - 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, non-racemic spacers.
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U2 - 10.1002/chem.200401253
DO - 10.1002/chem.200401253
M3 - Article
C2 - 15674978
AN - SCOPUS:17444411162
SN - 0947-6539
VL - 11
SP - 2284
EP - 2294
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 8
ER -