The direct introduction of carbonates α to carbonyl groups

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

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13 Citations (Scopus)

Abstract

The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.
Original languageUndefined/Unknown
Pages (from-to)3435-3438
Number of pages4
JournalSynlett
Issue number20
DOIs
Publication statusPublished - 2006

Keywords

  • α-oxycarbonates
  • carbonyl groups
  • hydrochloride reagents

Cite this

Hall, A., Jones, K. L., Jones, T. C., Killeen, N. M., Porzig, R., Taylor, P. H., ... Tomkinson, N. C. O. (2006). The direct introduction of carbonates α to carbonyl groups. Synlett, (20), 3435-3438. https://doi.org/10.1055/s-2006-956473