Application of a 2-methylenetetrahydropyran linchpin for the synthesis of 2,6-disubstituted 4H-pyrans

[Display omitted] •Linchpin approach to 2,6-disubstituted-4H-pyrans facilitates rapid diversification.•Mild reaction conditions and operationally simple reaction protocols.•Reactivity of 6-methylene-2-dihydropyrans is explored.•Target 4H-pyrans isolated in synthetically useful yields. A convergent,...

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Bibliographic Details
Published inTetrahedron letters Vol. 142; p. 155053
Main Authors Hasan, Md. Abid, Saunders, Laura J., Lam, Troy, Totah, Nancy I.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 06.06.2024
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Summary:[Display omitted] •Linchpin approach to 2,6-disubstituted-4H-pyrans facilitates rapid diversification.•Mild reaction conditions and operationally simple reaction protocols.•Reactivity of 6-methylene-2-dihydropyrans is explored.•Target 4H-pyrans isolated in synthetically useful yields. A convergent, modular approach for the synthesis of 2,6-disubstitued-4H-pyrans is reported via the sequential carbonyl ene reaction of a 2-methylenetetrahydropyran linchpin. This sequence proceeds under mild conditions in synthetically useful yields and highlights the utility of cross-oriented dienol ether derivatives as neutral nucleophiles in carbon–carbon bond forming reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2024.155053