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2005
Carbohydrates
U 0500
Enantioselective Synthesis of Tetrafluoroethylene-Containing Monosaccharides.
A straightforward synthesis of a furanose (VII), a pyranose (X) and a glycal (XI)
07- 197 —
containing a tetrafluoroethylene unit is presented using a fluorinated-building-block
approach. The approach starts with the asymmetric Sharpless dihydroxylation of a terminal tetrafluorinated alkene (I) followed by an appropriate cyclization step. A novel
domino perfluoroalkyl radical addition—atom transfer—nucleophilic cyclization reaction is developed for the formation of the pyranose ring (X). — (BOYDELL, A. J.;
VINADER, V.; LINCLAU*, B.; Angew. Chem., Int. Ed. 43 (2004) 42, 5677-5679;
Dep. Chem., Univ. Southampton, Southampton SO17 1BJ, UK; Eng.) — Mischke
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