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

Scope and limitation of AD reactions of terminally difluorinated dienes illustrative of de novo asymmetric synthesis of a xylulose analogue. Readily available difluoroenol iodides and stannanes undergo palladium-catalysed coupling reactions with alkenylstannanes and iodides, respectively, to afford...

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Published inTetrahedron: asymmetry Vol. 16; no. 2; pp. 347 - 359
Main Authors Cox, Liam R., DeBoos, Gareth A., Fullbrook, Jeremy J., Percy, Jonathan M., Spencer, Neil
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.01.2005
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
YEAST
PYRIDOXINE
REAGENTS
BIOSYNTHESIS
VITAMIN-B-6
CHEMISTRY
CONTAINING BUILDING-BLOCKS
STEREOSELECTIVE-SYNTHESIS
TITRATION
INCORPORATION PATTERN
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Summary:Scope and limitation of AD reactions of terminally difluorinated dienes illustrative of de novo asymmetric synthesis of a xylulose analogue. 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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.11.017