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

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


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
Issue number20
Publication statusPublished - 2006


  • α-oxycarbonates
  • carbonyl groups
  • hydrochloride reagents

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