Djojo F, Ravanelli E, Vostrowsky O, Hirsch A (2000)
Publication Type: Journal article, Original article
Publication year: 2000
Original Authors: Djojo F., Ravanelli E., Vostrowsky O., Hirsch A.
Publisher: Wiley-VCH Verlag
Pages Range: 1051-1059
Journal Issue: 6
URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-0034057345&origin=inward
The facile synthesis of enantiomerically pure C-symmetrical fullerene dendrimers all-R-(f)A-7, all-S-(f)C-8, all-R-(f)C-9, and all-S-(f)A-10, as well as lipofullerenes all-S-(f)A-11 and all-S-(f)C-12 involving an octahedral [3:3] addition pattern is described. The C symmetrical tris[bis(4-phenyl-2-oxazoline)methano]-fullerenes 1, 2, 3, and 4 with known absolute configuration were used as precursors. The completion of the octahedral addition pattern was achieved by a threefold cyclopropanation with the dendritic 3,5-dihydroxybenzylic bromomalonate 5 and the lipophilic dioctadecyl bromomalonate 6. The absolute configurations of the precursor trisadducts were retained in the inherently chiral C-symmetrical hexakisadducts 7-12. The structure and the isomeric purity of all hexakisadducts 7-12 were unambiguously proven by NMR spectroscopy and other techniques. Preliminary experiments with the dendritic hexakisadducts all-S- (f)C 8 and all-S-(f)A 10 revealed that these macromolecular ligands posess catalytic properties with respect to stereoselective cyclopropanations of styrene with ethyl diazoacetate.
APA:
Djojo, F., Ravanelli, E., Vostrowsky, O., & Hirsch, A. (2000). Fullerene dendrimers and lipofullerenes with an inherently chiral hexaaddition pattern. European Journal of Organic Chemistry, 6, 1051-1059.
MLA:
Djojo, Francis, et al. "Fullerene dendrimers and lipofullerenes with an inherently chiral hexaaddition pattern." European Journal of Organic Chemistry 6 (2000): 1051-1059.
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