Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: a 1,1-difluoro-1-deoxy-d-xylulose |
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| Affiliation: | 1. School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, United Kingdom;2. Avecia Ltd, Hexagon House, PO Box 42, Blackley, Manchester M9 8ZS, United Kingdom;3. Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, United Kingdom;1. School of Chemical Sciences, University of Chinese Academy of Sciences, No. 19A, Yuquan Road, Beijing, 100049, PR China;2. College of Earth and Planetary Sciences, University of Chinese Academy of Sciences, Key Laboratory of Computational Geodynamics, Chinese Academy of Sciences, Beijing, 100049, PR China;1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan;1. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior S/N, Cd. Universitaria, C.P. 04510 México, D.F., Mexico;2. Instituto de Investigaciones en Materiales, Unidad Morelia, Universidad Nacional Autónoma de México, Campus Morelia UNAM, Antigua Carretera a Pátzcuaro No. 8701, Col. Ex-Hacienda de San José de la Huerta, C.P. 58190 Morelia, Michoacán, Mexico |
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| 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. |
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