A general method for the alpha-acyloxylation of carbonyl compounds |
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Authors: | Beshara Cory S Hall Adrian Jenkins Robert L Jones Kerri L Jones Teyrnon C Killeen Niall M Taylor Paul H Thomas Stephen P Tomkinson Nicholas C O |
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Affiliation: | School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, UK. |
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Abstract: | [chemical reaction: see text]. A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is regiospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates. |
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