New reagents for the metal-free one-pot alpha-functionalisation of carbonyl compounds

Teyrnon C. Jones, Niall M. Killeen, Kerri L. Jones, Nicholas C. O. Tomkinson, Adrian. Hall

Research output: Contribution to journalConference Contribution


This poster describes the scope and features of some new methods for the metal-free α-functionalisation of carbonyl compds. (Figure 1). A new family of reagents 1 based on an N-alkyl hydroxylamine skeleton are shown to react with both aldehydes and cyclic and acyclic ketones to generate α-functionalised products under mild conditions and in good yield. Reactions proceed in one practical step in the presence of both air and moisture, and are tolerant of a wide variety of functional groups. Addnl., in the case of non-sym. substrates the reaction proceeds with excellent regioselectivity. The reagents presented can be used to effect the first direct conversion of carbonyl compds. to α-oxy carbamates, carbonates and tosylates amongst others, and offer a valuable new technique for the synthetic chemist's toolbox. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)365-ORGN
JournalAbstracts of papers - American Chemical Society
Publication statusPublished - 2006
Event231st National Meeting of the American-Chemical-Society - Atlanta, GA , United States
Duration: 26 Mar 200630 Mar 2006


  • new reagents
  • metal-free
  • one-pot
  • alpha-functionalisation
  • carbonyl compounds

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