Asymmetric oxidation of enol phosphates to α-hydroxy ketones by (salen)manganese(III) complex. Effects of the substitution pattern of enol phosphates on the stereochemistry of oxygen transfer |
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Authors: | Marek Koprowski, Jerzy uczak,Ewa Krawczyk |
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Affiliation: | aCentre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland |
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Abstract: | This paper presents a study of enantioselective catalytic oxidation of a variety of differently substituted, cyclic (E) and acyclic (Z)-enol phosphates. The asymmetric oxidation of acyclic (Z)-enol phosphates containing alkoxy substituents in the phosphate group 2a, c, e–g, i, and j and Z-configured enol phosphates containing aryloxy substituents in the phosphate group 2b, d, and h afforded optically active α-hydroxy ketones 4a–j of opposite configuration with good to high enantioselectivity. The influence of electronic and steric effects of the enol phosphate substituents on the stereoselectivity of oxidation was studied. |
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Keywords: | Enol phosphates Asymmetric oxidation α -Hydroxy ketones Jacobsen's catalyst |
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