Issue 42, 2011
From the journal:

Chemical Communications

Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters†

Marsewi Ngatimin,a   Raphael Frey,b   Cecily Andrews,b   David W. Lupton*a  and  Oliver E. Hutt*b  

* Corresponding authors

a School of Chemistry, Monash University, Clayton, Melbourne, Australia
E-mail: david.lupton@monash.edu
Fax: 613 9905 4597
Tel: 613 9902 0327

b CSIRO Materials Science and Engineering, Bag 10, Clayton South MDC, Australia
E-mail: oliver.hutt@csiro.au
Fax: 613 9545 2446
Tel: 613 9545 2580

Abstract

Vinylogous esters bearing para or metamethoxy benzyl groups undergo oxidative cyclisation with 5–20 mol% iodobenzene and m-CPBA to give spirofuran or benzopyran containing heterocycles. The reaction allows rapid generation of skeletal complexity in good to excellent yields via a novel oxidative cyclisation.

Graphical abstract: Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters

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Article information

DOI
https://doi.org/10.1039/C1CC15015D
Article type
Communication
Submitted
12 Aug 2011
Accepted
08 Sep 2011
First published
26 Sep 2011

Chem. Commun., 2011,47, 11778-11780

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Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters

M. Ngatimin, R. Frey, C. Andrews, D. W. Lupton and O. E. Hutt, Chem. Commun., 2011, 47, 11778 DOI: 10.1039/C1CC15015D

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