Issue 19, 2011
From the journal:

Organic & Biomolecular Chemistry

Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: Steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones†‡

Rema B. Devi,a   Matthias Henrot,a   Michaël De Paolis*a  and  Jacques Maddalunoa  

* Corresponding authors

a Laboratoire des Fonctions Azotées et Oxygénées Complexes de l'IRCOF, CNRS UMR 6014 & FR 3038, Université de Rouen, Mont Saint-Aignan, France
E-mail: michael.depaolis@univ-rouen.fr
Fax: (+33) 2 35 52 29 71

Abstract

An unprecedented domino synthesis of tetrahydrobenzofuran-4-ones is described implicating chemoselective alkylation of various 1,3-cyclohexanediones with bromocrotonate or crotonitrile followed by oxa-Michael cyclization. Further transformations of this core to reach molecular diversity are also presented.

Graphical abstract: Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: Steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones

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Article information

DOI
https://doi.org/10.1039/C1OB05923H
Article type
Communication
Submitted
08 Jun 2011
Accepted
05 Jul 2011
First published
05 Jul 2011

Org. Biomol. Chem., 2011,9, 6509-6512

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Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: Steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones

R. B. Devi, M. Henrot, M. De Paolis and J. Maddaluno, Org. Biomol. Chem., 2011, 9, 6509 DOI: 10.1039/C1OB05923H

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