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Synthesis 2015; 47(08): 1076-1084
DOI: 10.1055/s-0034-1380160
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© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Intermolecular [5+1] and [5+2] Cycloadditions Using 1,4-Enynes with an Electron-Donating Ester on the 3-Position

Casi M. Schienebeck
a   School of Pharmacy, University of Wisconsin, Madison, WI 53706, USA
,
Wangze Song
a   School of Pharmacy, University of Wisconsin, Madison, WI 53706, USA
,
Angela M. Smits
a   School of Pharmacy, University of Wisconsin, Madison, WI 53706, USA
,
Weiping Tang*
a   School of Pharmacy, University of Wisconsin, Madison, WI 53706, USA
b   Department of Chemistry, University of Wisconsin, Madison, WI 53705, USA   Email: wtang@pharmacy.wisc.edu
› Author Affiliations
Further Information

Publication History

Received: 17 November 2014

Accepted after revision: 22 January 2015

Publication Date:
02 March 2015 (online)

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Abstract

Various 3-acyloxy-1,4-enynes could be employed in rhodium-catalyzed intermolecular [5+1] and [5+2] cycloadditions with CO or alkynes, respectively. The rate of these cycloadditions could be accelerated significantly by using 1,4-enynes with an electron-donating ester on the 3-position. The scope of rhodium-catalyzed [5+1] and [5+2] cy­cloadditions were examined by using 1,4-enynes bearing an electron-donating ester.

1 Introduction

2 Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition

3 Rhodium-Catalyzed Intermolecular [5+1] Cycloaddition

4 Conclusion

Key words

catalysis - cycloaddition - rhodium - rings - benzene

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380160.
  • Supporting Information
 

  • References

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