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

Authors

  • 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
Weitere Informationen

Publikationsverlauf

Received: 17. November 2014

Accepted after revision: 22. Januar 2015

Publikationsdatum:
02. März 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

Supporting Information