Issue 18, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric α-oxyacylation of cyclic ketones†

Deborah A. Smithen,*a   Christopher J. Mathewsb  and  Nicholas C. O. Tomkinson*c  

* Corresponding authors

a School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, UK

b Chemistry Department, Syngenta, Jealotts Hill International Research Centre, Bracknell, Berkshire, UK

c WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde, 295 Cathedral Street, Glasgow, UK
E-mail: Nicholas.Tomkinson@strath.ac.uk
Fax: +44(0)141 548 5743
Tel: +44(0)141 548 2276

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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Article information

DOI
https://doi.org/10.1039/C2OB25293G
Article type
Paper
Submitted
09 Feb 2012
Accepted
09 Mar 2012
First published
12 Mar 2012

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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