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Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates

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Abstract

An expedient synthesis of highly substituted tetrahydrobenzofuran via an unsymmetrical silyloxyallyl cation is reported. Conveniently generated under catalytic Brønsted acid conditions, nucleophilic capture of this reactive intermediate by silylenolate, followed by Paal–Knorr cascade cyclization in the presence of tosic acid monohydrate effectively constructed the tetrahydrobenzofuran core in a single synthetic step.

Graphical abstract: Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates

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Article information


Submitted
08 Mar 2020
Accepted
24 Mar 2020
First published
26 Mar 2020

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

Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates

F. O. Badmus, J. A. Malone, F. R. Fronczek and R. Kartika, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01796E

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