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Synlett 2001; 2001(Special Issue): 0955-0959
DOI: 10.1055/s-2001-14632
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Studies on the Synthesis of 2,6-Disubstituted Dihydropyrans: Intervention of Oxonia-Cope Rearrangements in the Lewis Acid Mediated Cyclodehydrative Reactions of Aldehydes and β-Hydroxyallylsilanes

William R. Roush* , Garrett J. Dilley
  • *Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA; Fax + 1 734 6 47 92 79; E-mail: roush@umich.edu
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Publikationsdatum:
31. Dezember 2001 (online)

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The dehydrative coupling reactions of anti-β-hydroxyallylsilanes 5 and aldehydes provide 2,6-dihydropyrans 27 by pathways involving oxonium ions that cyclize via boat-like transition state 21, with the intervention of oxonia-Cope rearrangements (21 → 29).

addition reactions - intramolecular allylations - sigmatropic rearrangement - allylsilanes - dihydropyrans