Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: a 1,1-difluoro-1-deoxy-D-xylulose

Liam R Cox, Gareth A DeBoos, Jeremy J Fullbrook, Jonathan Percy, Neil Spencer

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11 Citations (Scopus)

Abstract

Readily available difluoroenol iodides and stannanes undergo palladium-catalysed coupling reactions with alkenylstannanes and iodides, respectively, to afford a trial set of difluorinated 1,3- and 1,4-dienes, which were then exposed to AD conditions. A number of issues were raised including generally low reactivity of simple 1,3-butadienes, and useful reactivity of certain 1,4- and substituted 1,3-pentadienes. Though the basic conditions used for the AD resulted in the decomposition of certain diol products, enol acetal chemistry allowed the asymmetric synthesis of a difluorinated analogue of a deoxyxylulose.
Original languageEnglish
Pages (from-to)347-359
Number of pages13
JournalTetrahedron: Asymmetry
Volume16
Issue number2
DOIs
Publication statusPublished - 2005

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Keywords

  • asymmetric dihydroxylation
  • difluorinated carbohydrate analogues

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