Cox, Liam R and DeBoos, Gareth A and Fullbrook, Jeremy J and Percy, Jonathan and Spencer, Neil (2005) Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: a 1,1-difluoro-1-deoxy-D-xylulose. Tetrahedron: Asymmetry, 16 (2). pp. 347-359. ISSN 0957-4166Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||asymmetric dihydroxylation , difluorinated carbohydrate analogues, Chemistry, Organic Chemistry, Catalysis, Physical and Theoretical Chemistry, Inorganic Chemistry|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Pure Administrator|
|Date Deposited:||04 Apr 2012 19:56|
|Last modified:||27 Apr 2016 18:26|