Issue 32, 2011
From the journal:

Chemical Communications

2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation†

Ozora Kubo,a   Kenzo Yahata,a   Tomohiro Maegawaa  and  Hiromichi Fujioka*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, Japan
E-mail: fujioka@phs.osaka-u.ac.jp
Fax: +81 668798229
Tel: +81 668798225

Abstract

A diastereoselective ring contraction of the diastereomixture of 2,4-disubstituted 1,3-dioxepins to 2,5-cis-2,3,5-trisubstituted tetrahydrofurans was achieved using TfOH in DMF. The reaction appears to proceed via a chair-like transition state, in which stereomutation of the oxocarbenium occurred, followed by an aldol-type cyclization.

Graphical abstract: 2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation

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Article information

DOI
https://doi.org/10.1039/C1CC12934A
Article type
Communication
Submitted
19 May 2011
Accepted
27 Jun 2011
First published
11 Jul 2011

Chem. Commun., 2011,47, 9197-9199

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2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation

O. Kubo, K. Yahata, T. Maegawa and H. Fujioka, Chem. Commun., 2011, 47, 9197 DOI: 10.1039/C1CC12934A

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