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Issue 100, 2020
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Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

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Abstract

A formal hydroxylation/cyclization of cyclopropanemethanols with DMSO is described, which involves isomerization and cyclization under Tf2O catalysis. This reaction undergoes ring-opening of the cyclopropane moiety to generate homoallylic alcohols, which react with DMSO to produce 3-benzylidenetetrahydrofurans. With various substituted groups on cyclopropanemethanols the reactions proceed smoothly and the desired 3-benzylidenetetrahydrofurans are obtained in moderate to good yields.

Graphical abstract: Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

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Article information


Submitted
21 Oct 2020
Accepted
18 Nov 2020
First published
19 Nov 2020

Chem. Commun., 2020,56, 15627-15630
Article type
Communication

Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

Z. Qi, H. Wang, Y. Ren, Y. Niu, Y. Jiang and R. Yan, Chem. Commun., 2020, 56, 15627
DOI: 10.1039/D0CC07002E

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