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The Direct Introduction of Carbonates α to Carbonyl Groups

Adrian Hall, Kerri L. Jones, Teyrnon C. Jones, Niall M. Killeen, Robert P÷rzig, Paul H. Taylor, Sze Chak Yau, Nicholas C. O. Tomkinson*

*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK, Email:

A. Hall, K. L. Jones, T. C. Jones, N. M. Killeen, R. P÷rzig, P. H. Taylor, S. C. Yau, N. C. O. Tomkinson, Synlett, 2006, 3435-3438.

DOI: 10.1055/s-2006-956473


Bench stable N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepared in two high-yielding steps from N-Boc-N-methyl hydroxylşamine. Subsequent reaction with various carbonyl compounds give the corresponding α-functionalised products in good yield via a proposed [3,3]-sigmatropic rearrangement.

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Key Words

metal-free synthesis, hydroxylamines, carbonates, α-hydroxylation

ID: J60-Y2006-4830