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Issue 18, 2012
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Asymmetric α-oxyacylation of cyclic ketones

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Abstract

Reaction of cyclic ketones with chiral N-alkyl-O-acyl hydroxylamines leads to the corresponding α-oxyacylated carbonyl compound in up to 89% ee. The levels of asymmetric induction were influenced by solvent polarity, acid strength and, to a lesser extent, temperature. Increasing the steric bulk around the nitrogen atom of the hydroxylamine reagent led to increased levels of asymmetric induction, which was also found to be detrimental to the yield observed for the transformation. Examination of N- and O-substituents along with substrates revealed the scope and limitations of the procedure.

Graphical abstract: Asymmetric α-oxyacylation of cyclic ketones

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Publication details

The article was received on 09 Feb 2012, accepted on 09 Mar 2012 and first published on 12 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25293G
Citation: Org. Biomol. Chem., 2012,10, 3756-3762
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    Asymmetric α-oxyacylation of cyclic ketones

    D. A. Smithen, C. J. Mathews and N. C. O. Tomkinson, Org. Biomol. Chem., 2012, 10, 3756
    DOI: 10.1039/C2OB25293G

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