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)]
|Journal||Abstracts of papers - American Chemical Society|
|Publication status||Published - 2006|
|Event||231st National Meeting of the American-Chemical-Society - Atlanta, GA , United States|
Duration: 26 Mar 2006 → 30 Mar 2006
- new reagents
- carbonyl compounds
Jones, T. C., Killeen, N. M., Jones, K. L., Tomkinson, N. C. O., & Hall, A. (2006). New reagents for the metal-free one-pot alpha-functionalisation of carbonyl compounds. Abstracts of papers - American Chemical Society, 231, 365-ORGN.