Journal
SYNLETT
Volume -, Issue 11, Pages 1523-1526Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260776
Keywords
alkynes; domino reaction; gold catalysis; heterocycles; rearrangement
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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Starting from pentanediol various oct-6-yne-1,5-diols were prepared. In the presence of catalytic amounts of an Au(I) or Pt(II) catalyst transformation to cis-2,6-tetrahydropyrans was observed. It is assumed that this novel domino sequence proceeds via an initial Meyer-Schuster rearrangement of the propargylic alcohol yielding a hydroxyenone that undergoes an intramolecular oxa-Michael addition through a chairlike transition state to the tetrahydropyran system.
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