2,6-Disubstituted Tetrahydropyrans
by Domino Meyer-Schuster Rearrangement-Hetero-Michael
Addition of 6-Alkyne-1,5-diols

Max Wohland; Martin E. Maier

doi:10.1055/s-0030-1260776

LETTER

2,6-Disubstituted Tetrahydropyrans by Domino Meyer-Schuster Rearrangement-Hetero-Michael Addition of 6-Alkyne-1,5-diols

Max Wohland, Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen
Fax: +49(7071)295137; e-Mail: martin.e.maier@uni-tuebingen.de;

Abstract

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Abstract

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.

Key words

alkynes - domino reaction - gold catalysis - heterocycles - rearrangement

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Referenzen

References and Notes

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