New methods in metal-free organic synthesis: a practical procedure for carbonyl α-oxidation

Teyrnon C. Jones, Nicholas C. O. Tomkinson

Research output: Contribution to conferencePaper


The development of metal-free transformations in org. synthesis offers significant potential economic and environmental benefits, particularly in the context of industrial processes. We have developed a novel family of org. reagents which react with carbonyl compds. to furnish α-oxygenated products: important synthetic building blocks more commonly accessed via air-sensitive metal intermediaries. Here, we report that N-alkyl-O-acyl hydroxylamine salts 1 react with both cyclic and acyclic carbonyl compds. to furnish α-oxyacylated products under ambient conditions in the presence of air and moisture. This very practical one step technique is tolerant of a wide variety of functional groups, shows remarkable regioselectivity and proceeds via a proposed [3,3]-sigmatropic rearrangement (Figure 1). As well as discussing the scope of this novel reaction we will relate our current findings on the reaction mechanism, as well as our efforts to make the procedure both catalytic and asym., adding to the new wave of organocatalytic transformations. [on SciFinder(R)]
Original languageEnglish
Publication statusPublished - Mar 2006
Event231st ACS National Meeting - Atlanta, GA, United States
Duration: 26 Mar 200630 Mar 2006


Conference231st ACS National Meeting
Country/TerritoryUnited States
CityAtlanta, GA


  • new methods
  • metal-free
  • organic synthesis
  • practical procedure
  • carbonyl α-oxidation
  • carbonyl


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