New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine |
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| Institution: | 1. Department of Chemistry, University of Puerto Rico, PO Box 23346, U.P.R. Station, San Juan 00931-3346, Puerto Rico;2. Department of Cell Biology and Neuroscience, University of California at Riverside, CA 92521, USA;1. College of Materials Science and Engineering, Jilin University, Changchun 130022, PR China;2. Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China;3. Shangdong Non-Metallic Materials Institute, Jinan 250000, PR China;1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic;2. Institute of Environmental and Chemical Engineering, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic |
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| Abstract: | The reduction of α- or β-ketophosphonates with a chiral reactant 1, prepared from sodium borohydride and (R)- or (S)-tartaric acids, led to the formation of both (S)- and (R)-α- or β-hydroxyphosphonates in high yields. The stereoselectivity of the reaction depended on the absolute configurations of 1 and the ketophosphonates. The reduction of di(1R,2S,5R)-menthyl ketophosphonates with (R)-1 proceeded with matched double asymmetric induction to give high diastereomeric excesses of hydroxyphosphonates (up to 96% de). This methodology was used for the preparation of enantiomerically pure phosphonate modified carnitine on a multigram scale. |
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