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Synthesis of trans ‐1, trans ‐2, trans ‐3, and trans ‐4 Bisadducts of C 60 by Regio‐ and Stereoselective Tether‐Directed Remote Functionalization
Author(s) -
Sergeyev Sergey,
Schär Michael,
Seiler Paul,
Lukoyanova Olena,
Echegoyen Luis,
Diederich François
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401253
Subject(s) - regioselectivity , stereoselectivity , chemistry , fullerene , stereochemistry , double bond , base (topology) , cis–trans isomerism , organic chemistry , catalysis , mathematical analysis , mathematics
The double Bingel reaction of fullerene C 60 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.