Synthesis of α-hydroxy ketones from terpene aldehydes

Research output: Contribution to journal › Article › Research › peer review

Authors

  • Martin Schueler
  • Holger Zorn
  • Alexandra M.Z. Slawin
  • Ralf G. Berger

Research Organisations

External Research Organisations

  • University of St. Andrews
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Details

Original languageEnglish
Pages (from-to)2591-2600
Number of pages10
JournalSynthetic communications
Volume34
Issue number14
Publication statusPublished - 2004

Abstract

Unsymmetrically substituted α-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to α,β-unsaturated aldehydes and afforded the respective α-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric α-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

Keywords

    α-Hydroxy ketones, Acyloins, Camphanates, Copper salt catalysis, Cyanohydrin trimethylsilyl ethers, Grignard reaction, Nitriles, Tautomerisation, Terpene aldehydes

ASJC Scopus subject areas

Cite this

Synthesis of α-hydroxy ketones from terpene aldehydes. / Schueler, Martin; Zorn, Holger; Slawin, Alexandra M.Z. et al.
In: Synthetic communications, Vol. 34, No. 14, 2004, p. 2591-2600.

Research output: Contribution to journal › Article › Research › peer review

Schueler, M, Zorn, H, Slawin, AMZ & Berger, RG 2004, 'Synthesis of α-hydroxy ketones from terpene aldehydes', Synthetic communications, vol. 34, no. 14, pp. 2591-2600. https://doi.org/10.1081/SCC-200025618
Schueler, M., Zorn, H., Slawin, A. M. Z., & Berger, R. G. (2004). Synthesis of α-hydroxy ketones from terpene aldehydes. Synthetic communications, 34(14), 2591-2600. https://doi.org/10.1081/SCC-200025618
Schueler M, Zorn H, Slawin AMZ, Berger RG. Synthesis of α-hydroxy ketones from terpene aldehydes. Synthetic communications. 2004;34(14):2591-2600. doi: 10.1081/SCC-200025618
Schueler, Martin ; Zorn, Holger ; Slawin, Alexandra M.Z. et al. / Synthesis of α-hydroxy ketones from terpene aldehydes. In: Synthetic communications. 2004 ; Vol. 34, No. 14. pp. 2591-2600.
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T1 - Synthesis of α-hydroxy ketones from terpene aldehydes

AU - Schueler, Martin

AU - Zorn, Holger

AU - Slawin, Alexandra M.Z.

AU - Berger, Ralf G.

PY - 2004

Y1 - 2004

N2 - Unsymmetrically substituted α-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to α,β-unsaturated aldehydes and afforded the respective α-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric α-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

AB - Unsymmetrically substituted α-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to α,β-unsaturated aldehydes and afforded the respective α-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric α-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

KW - α-Hydroxy ketones

KW - Acyloins

KW - Camphanates

KW - Copper salt catalysis

KW - Cyanohydrin trimethylsilyl ethers

KW - Grignard reaction

KW - Nitriles

KW - Tautomerisation

KW - Terpene aldehydes

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DO - 10.1081/SCC-200025618

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JO - Synthetic communications

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