Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via an intramolecular bismuth-mediated oxa-conjugate addition reaction

The intramolecular oxa-conjugate addition of tethered triethylsilyloxy substituted α,β-unsaturated ketones mediated by bismuth(III) nitrate pentahydrate provides a mild and efficient method for the stereoselective construction of cis-2,6-disubstituted tetrahydropyrans. The intramolecular oxa-conjuga...

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Veröffentlicht in:Tetrahedron letters 2005-08, Vol.46 (34), p.5625-5627
Hauptverfasser: Evans, P. Andrew, Andrews, William J.
Format: Artikel
Sprache:eng
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Zusammenfassung:The intramolecular oxa-conjugate addition of tethered triethylsilyloxy substituted α,β-unsaturated ketones mediated by bismuth(III) nitrate pentahydrate provides a mild and efficient method for the stereoselective construction of cis-2,6-disubstituted tetrahydropyrans. The intramolecular oxa-conjugate addition of tethered triethylsilyloxy substituted α,β-unsaturated ketones mediated by bismuth(III) nitrate pentahydrate provides a mild and efficient method for the stereoselective construction of cis-2,6-disubstituted tetrahydropyrans.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.06.100