Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses

Caravano, Audrey and Field, Robert A. and Percy, Jonathan M. and Rinaudo, Giuseppe and Roig, Ricard and Singh, Kuldip. (2009) Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses. Organic and Biomolecular Chemistry, 7 (5). pp. 996-1008. ISSN 1477-0520 (

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Free radical bromination and nucleophilic fluorination allows the conversion of Me sorbate into the 6-fluoro analog which undergoes sequential asym. dihydroxylation reactions. A range of 6-deoxy-6-fluoro-sugars were prepd. by using different combinations of ligands. While the enantiomeric excesses obtained were comparable to those from other 6-substituted sorbates, the regioselectivity of dihydroxylation was moderate, with both 2,3- and 4,5-diols being obtained. A successful temporary persilylation strategy was evolved to convert the products of dihydroxylation rapidly to the fluoro-sugars 6-deoxy-6-fluoro-L-idose, 6-fluoro-L-fucose and 6-deoxy-6-fluoro-D-galactose, which were obtained in overall yields of 4%, 6% and 8% from Me 6-fluoro-hexa-2E,4E-dienoate.