Issue 19, 2011
From the journal:

Chemical Communications

Unexpected C–C bond cleavage of epoxide motif: Rhodium(i)-catalyzed tandem heterocyclization/[4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones†

Tao Wang,a   Cui-Hong Wanga  and  Junliang Zhang*a  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P.R. China
E-mail: jlzhang@chem.ecnu.edu.cn
Fax: (+86) 21-6223-5039

Abstract

A rhodium(I)-catalyzed tandem heterocyclization and formal [4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones was developed, which provides a general, efficient and practical route to highly substituted furo[3,4-b]furan-3(2H)-ones, wherein the epoxide motif undergo unexpected C–C bond cleavage rather than the classical C–O bond cleavage.

Graphical abstract: Unexpected C–C bond cleavage of epoxide motif: Rhodium(i)-catalyzed tandem heterocyclization/[4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones

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Article information

DOI
https://doi.org/10.1039/C0CC05650B
Article type
Communication
Submitted
17 Dec 2010
Accepted
23 Mar 2011
First published
06 Apr 2011

Chem. Commun., 2011,47, 5578-5580

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Unexpected C–C bond cleavage of epoxide motif: Rhodium(I)-catalyzed tandem heterocyclization/[4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones

T. Wang, C. Wang and J. Zhang, Chem. Commun., 2011, 47, 5578 DOI: 10.1039/C0CC05650B

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