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Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans

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Abstract

A general [5+1] annulation reaction, which utilized 4-bromo- or 4-mesyloxy-but-2-enyl peroxides as unique five-atom bielectrophilic synthons to participate in the C–C and the subsequent umpolung C–O bond-forming reactions with C1 nucleophiles, has been developed for the facile synthesis of 2,2-disubstituted dihydropyrans in high yields under mild basic conditions. The dihydropyrans, which are readily prepared on a gram scale by this new method, can be flexibly transformed into the biologically important tetrahydropyrans and pyranones in 1–2 steps.

Graphical abstract: Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans

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Article information


Submitted
15 Aug 2020
Accepted
21 Sep 2020
First published
06 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans

C. Zhong, Q. Yin, Y. Zhao, Q. Li and L. Hu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05565D

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