Three-step synthesis of chiral and sterically hindered amino alcohols based on cyclic enol phosphates |
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| Authors: | Krzysztof Owsianik Ewa Krawczyk Grażyna Mielniczak Marek Koprowski Lesław Sieroń |
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| Institution: | 1. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363, ?ód?, Poland;2. Institute of General and Ecological Chemistry, Department of Chemistry, Lodz University of Technology, ?eromskiego 116, 90-924, ?ód?, Poland |
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| Abstract: | The new synthesis of chiral and sterically hindered 1,2-amino alcohols derivatives of 2-methyl-indane and 1,2,3,4-tethrahydrophenanthrene based on cyclic enol phosphates were investigated. The desired products were obtained using three step procedure: oxidation of accessible enol phosphates, transformation α-hydroxy ketones into corresponding oximes and finally reduction of the last one to 1,2-amino alcohols. The optimal conditions of all stages to obtain products with high enantioselectivity or diastereomeric ratio were found and elaborated. The structures and absolute configurations of (3R)-2,3-dihydro-3-hydroxy-1H-phenanthren-4-one and corresponding oxime were confirmed by X-ray analysis. |
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| Keywords: | Enol phosphates 1 2-amino alcohols α-Hydroxy ketones α-Hydroxy oximes Enantioselective synthesis |
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