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

作者：Cox LR; DeBoos GA; Fullbrook JJ; Percy JM^*; Spencer N

来源：Tetrahedron: Asymmetry , 2005, 16(2): 347-359.

DOI：10.1016/j.tetasy.2004.11.017

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.

• 出版日期2005-1-24