TY - JOUR
T1 - Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydratre analogues: a 1,1-difluoro-1-deoxy-D-xylulose
AU - Cox, Liam
AU - DeBoos, GA
AU - Fullbrook, JJ
AU - Percy, JM
AU - Spencer, Neil
PY - 2005/1/1
Y1 - 2005/1/1
N2 - 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. (C) 2004 Elsevier Ltd. All rights reserved.
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. (C) 2004 Elsevier Ltd. All rights reserved.
UR - http://www.scopus.com/inward/record.url?scp=12944278733&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2004.11.017
DO - 10.1016/j.tetasy.2004.11.017
M3 - Article
VL - 16
SP - 347
EP - 359
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 2
ER -