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

Jones, Teyrnon C. and Killeen, Niall M. and Jones, Kerri L. and Tomkinson, Nicholas C. O. and Hall, Adrian. (2006) New reagents for the metal-free one-pot alpha-functionalisation of carbonyl compounds. Abstracts of papers - American Chemical Society, 231. 365-ORGN. ISSN 0065-7727

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Abstract

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)]