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Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 1, pp 119–134 | Cite as

Gold(I)-catalyzed heterocyclization of β-alkynyl hydroxamic acids: synthesis of isoxazolidin-3-ones

  • Andreas P. Häring
  • Philipp Klahn
  • Martin Jübermann
  • Fabian Mohr
  • Stefan F. Kirsch
Original Paper

Abstract

A practical and mild method for the 5-exo cyclization of N-substituted α-alkynyl hydroxamic acids into isoxazolidin-3-ones catalyzed by Au(PPh3)SbF6 was developed. Under optimized conditions, the cyclization shows a high Z-selectivity for the newly formed exocyclic double bond.

Graphical Abstract

Keywords

Isoxazolidin-3-ones Heterocycles Catalysis Cyclizations Hydroxamic acid 

Notes

Acknowledgments

We are grateful to Deutsche Forschungsgemeinschaft (DFG; KI 1289/1–3) and Fonds der Chemischen Industrie (FCI) for financial support. The donation of chemicals by Rockwood Lithium is gratefully acknowledged.

Supplementary material

706_2014_1319_MOESM1_ESM.cif (14 kb)
Supplementary material 1 (CIF 14 kb)
706_2014_1319_MOESM2_ESM.cif (16 kb)
Supplementary material 2 (CIF 16 kb)
706_2014_1319_MOESM3_ESM.pdf (4 mb)
Supplementary material 3 (PDF 4049 kb)

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Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Andreas P. Häring
    • 1
  • Philipp Klahn
    • 1
  • Martin Jübermann
    • 1
  • Fabian Mohr
    • 2
  • Stefan F. Kirsch
    • 1
  1. 1.Bergische Universität Wuppertal, Fachbereich C, Organische ChemieWuppertalGermany
  2. 2.Bergische Universität Wuppertal, Fachbereich C, Anorganische ChemieWuppertalGermany

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