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

Research output: Contribution to journalArticle

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.
LanguageEnglish
Pages347-359
Number of pages13
JournalTetrahedron: Asymmetry
Volume16
Issue number2
DOIs
Publication statusPublished - 2005

Fingerprint

carbohydrates
Iodides
Carbohydrates
Butadiene
iodides
Palladium
reactivity
analogs
Decomposition
acetals
Acetals
dienes
synthesis
butadiene
palladium
chemistry
decomposition
products
1-deoxy-1,1-difluoro-D-xylulose
stannane

Keywords

  • asymmetric dihydroxylation
  • difluorinated carbohydrate analogues

Cite this

Cox, Liam R ; DeBoos, Gareth A ; Fullbrook, Jeremy J ; Percy, Jonathan ; Spencer, Neil. / Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: a 1,1-difluoro-1-deoxy-D-xylulose. In: Tetrahedron: Asymmetry. 2005 ; Vol. 16, No. 2. pp. 347-359 .
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Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: a 1,1-difluoro-1-deoxy-D-xylulose. / Cox, Liam R; DeBoos, Gareth A; Fullbrook, Jeremy J; Percy, Jonathan; Spencer, Neil.

In: Tetrahedron: Asymmetry, Vol. 16, No. 2, 2005, p. 347-359 .

Research output: Contribution to journalArticle

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AB - 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.

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