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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

Synlett (2001) (SPEC. ISS) 955-959
DOI: 10.1055/s-2001-14632
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Abstract

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

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Roush, W. R., & Dilley, G. J. (2001). 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. Synlett, (SPEC. ISS), 955–959. https://doi.org/10.1055/s-2001-14632

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