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

Audrey Caravano, Robert A. Field, Jonathan M. Percy, Giuseppe Rinaudo, Ricard Roig, Kuldip. Singh

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.
Original languageUndefined/Unknown
Pages (from-to)996-1008
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number5
DOIs
Publication statusPublished - 2009

Keywords

  • bromination
  • nucleophilic fluorination
  • ligands
  • dihydroxylation

Cite this

Caravano, A., Field, R. A., Percy, J. M., Rinaudo, G., Roig, R., & Singh, K. (2009). Developing an asymmetric, stereo-divergent route to selected 6-deoxy-6-fluoro-hexoses. Organic and Biomolecular Chemistry, 7(5), 996-1008. https://doi.org/10.1039/b815342f