Issue 26, 2013
From the journal:

Chemical Communications

Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes†

Casi M. Schienebeck,a   Patrick J. Robichaux,ab   Xiaoxun Li,a   Lianqing Chen*ac  and  Weiping Tang*ab  

* Corresponding authors

a School of Pharmacy, University of Wisconsin, Madison, WI, USA

b Department of Chemistry, University of Wisconsin, Madison, WI, USA

c Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission & Ministry of Education, South-Central University for Nationalities, Wuhan, China
E-mail: wtang@pharmacy.wisc.edu

Abstract

We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most terminal alkynes.

Graphical abstract: Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes

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Article information

DOI
https://doi.org/10.1039/C3CC40634B
Article type
Communication
Submitted
24 Jan 2013
Accepted
08 Feb 2013
First published
11 Feb 2013

Chem. Commun., 2013,49, 2616-2618

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Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes

C. M. Schienebeck, P. J. Robichaux, X. Li, L. Chen and W. Tang, Chem. Commun., 2013, 49, 2616 DOI: 10.1039/C3CC40634B

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