Issue 3, 2012
From the journal:

Organic & Biomolecular Chemistry

Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton†

Jane Totobenazara,a   Heloua Haroun,a   Julien Rémond,a   Karim Adil,b   Fabrice Dénès,c   Jacques Lebreton,c   Catherine Gaulon-Nourry*a  and  Pascal Gosselin*a  

* Corresponding authors

a Unité de Chimie Organique Moléculaire et Macromoléculaire – CNRS UMR 6011, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans, France
E-mail: catherine.gaulon@univ-lemans.fr, pascal.gosselin@univ-lemans.fr
Fax: +33 243 833 902
Tel: +33 243 833 371

b Laboratoire des Oxydes et Fluorures – CNRS UMR 6010, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans, France

c CEISAM – CNRS UMR 6230, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322 Nantes, France

Abstract

Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

Graphical abstract: Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

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Article information

DOI
https://doi.org/10.1039/C1OB06776A
Article type
Communication
Submitted
21 Oct 2011
Accepted
08 Nov 2011
First published
17 Nov 2011

Org. Biomol. Chem., 2012,10, 502-505

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Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

J. Totobenazara, H. Haroun, J. Rémond, K. Adil, F. Dénès, J. Lebreton, C. Gaulon-Nourry and P. Gosselin, Org. Biomol. Chem., 2012, 10, 502 DOI: 10.1039/C1OB06776A

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