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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

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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% 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