ORGN 365 |
| This poster describes the scope and features of some new methods for the metal-free α-functionalisation of carbonyl compounds (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. Additionally, in the case of non-symmetrical substrates the reaction proceeds with excellent regioselectivity. The reagents presented can be used to effect the first direct conversion of carbonyl compounds to α-oxy carbamates, carbonates and tosylates amongst others, and offer a valuable new technique for the synthetic chemist's toolbox.
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New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |
