ArticleThe Journal of organic chemistry2011
Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Lewis acid catalyzed spiro annulation of (RSC advances · 2023Article
- Synthesis of functionalised isochromans: epoxides as aldehyde surrogates in hexafluoroisopropanol.Chemical science · 2023Article
- Mechanism of Friedel-Crafts Acylation Using Metal Triflate in Deep Eutectic Solvents: An Experimental and Computational Study.ACS omega · 2023Article
- Article
- Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for AromaticJournal of the American Chemical Society · 2018Article
- Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.Organic letters · 2013Article
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Authors and funding
7 authors.
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Abstract
Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-δ-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)(3) were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)(3) and substrates providing TfOH in situ.
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