Issue 37, 2020
From the journal:

Chemical Communications

Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates†

Fatimat O. Badmus,a   Joshua A. Malone,a   Frank R. Fronczeka  and  Rendy Kartika ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803, USA
E-mail: rkartika@lsu.edu

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

DOI
https://doi.org/10.1039/D0CC01796E
Article type
Communication
Submitted
08 Mar 2020
Accepted
24 Mar 2020
First published
26 Mar 2020

Chem. Commun., 2020,56, 5034-5037

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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, 56, 5034 DOI: 10.1039/D0CC01796E

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