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 journalArticle

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.
LanguageUndefined/Unknown
Pages3435-3438
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
Hall, Adrian ; Jones, Kerri L. ; Jones, Teyrnon C. ; Killeen, Niall M. ; Porzig, Robert ; Taylor, Paul H. ; Yau, Sze Chak ; Tomkinson, Nicholas C. O. / The direct introduction of carbonates α to carbonyl groups. In: Synlett. 2006 ; No. 20. pp. 3435-3438.
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Hall, A, Jones, KL, Jones, TC, Killeen, NM, Porzig, R, Taylor, PH, Yau, SC & Tomkinson, NCO 2006, 'The direct introduction of carbonates α to carbonyl groups' Synlett, no. 20, pp. 3435-3438. https://doi.org/10.1055/s-2006-956473

The direct introduction of carbonates α to carbonyl groups. / Hall, Adrian; Jones, Kerri L.; Jones, Teyrnon C.; Killeen, Niall M.; Porzig, Robert; Taylor, Paul H.; Yau, Sze Chak; Tomkinson, Nicholas C. O.

In: Synlett, No. 20, 2006, p. 3435-3438.

Research output: Contribution to journalArticle

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T1 - The direct introduction of carbonates α to carbonyl groups

AU - Hall, Adrian

AU - Jones, Kerri L.

AU - Jones, Teyrnon C.

AU - Killeen, Niall M.

AU - Porzig, Robert

AU - Taylor, Paul H.

AU - Yau, Sze Chak

AU - Tomkinson, Nicholas C. O.

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AB - 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.

KW - α-oxycarbonates

KW - carbonyl groups

KW - hydrochloride reagents

U2 - 10.1055/s-2006-956473

DO - 10.1055/s-2006-956473

M3 - Article

SP - 3435

EP - 3438

JO - Synlett

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Hall A, Jones KL, Jones TC, Killeen NM, Porzig R, Taylor PH et al. The direct introduction of carbonates α to carbonyl groups. Synlett. 2006;(20):3435-3438. https://doi.org/10.1055/s-2006-956473