Picture of wind turbine against blue sky

Open Access research with a real impact...

The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

The Energy Systems Research Unit (ESRU) within Strathclyde's Department of Mechanical and Aerospace Engineering is producing Open Access research that can help society deploy and optimise renewable energy systems, such as wind turbine technology.

Explore wind turbine research in Strathprints

Explore all of Strathclyde's Open Access research content

Asymmetric alpha-oxyacylation of cyclic ketones

Smithen, Deborah and Mathews, Christopher and Tomkinson, Nick (2012) Asymmetric alpha-oxyacylation of cyclic ketones. Organic and Biomolecular Chemistry, 10 (18). pp. 3756-3762. ISSN 1477-0520

Full text not available in this repository. (Request a copy from the Strathclyde author)

Abstract

Reaction of cyclic ketones with chiral N-alkyl-O-acyl hydroxylamines leads to the corresponding α oxyacylated carbonyl compound in up to 89% e.e. 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 substrate revealed the scope and limitations of the procedure