- Asymmetric oxidation of enol phosphates to α-hydroxy ketones using Sharpless reagents and a fructose derived dioxirane
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The asymmetric oxidation of a variety of differently substituted, acyclic and cyclic enol phosphates using the Sharpless AD-reagents AD-mix-α and AD-mix-β, and a fructose derived chiral ketone as a catalyst, afforded the corresponding α-hydroxy ketones in high enantioselectivity and good yield. The influence of steric and electronic factors of the substrates on the facial stereoselectivity in the reported oxidations was studied.
- Krawczyk, Ewa,Mielniczak, Grazyna,Owsianik, Krzysztof,?uczak, Jerzy
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- Trifluoromethylation of allylsilanes under copper catalysis
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Branched allylic CF3 products are accessible by copper-catalyzed trifluoromethylation of allylsilanes with the Togni reagent I. The silyl group is critical to control the outcome of this reaction because in its absence, a product of addition be
- Mizuta, Satoshi,Galicia-Lopez, Oscar,Engle, Keary M.,Verhoog, Stefan,Wheelhouse, Katherine,Rassias, Gerasimos,Gouverneur, Veronique
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supporting information; experimental part
p. 8583 - 8587
(2012/08/14)
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- 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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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.
- Koprowski, Marek,?uczak, Jerzy,Krawczyk, Ewa
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p. 12363 - 12374
(2007/10/03)
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