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Synfacts 2010(5): 0556-0556
DOI: 10.1055/s-0029-1219670
DOI: 10.1055/s-0029-1219670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Stereoselective Ring Expansion of Vinyl Oxiranes
M. Brichacek, L. A. Batory, J. T. Njardarson*
Cornell University, Ithaca, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219670-1.jpg)
Significance
The described method allows for the stereoselective synthesis of cis- and trans-2,5-dihydrofurans from the corresponding matched vinyl oxirane. Many functional groups are well tolerated and the diastereoselectivities and yields are high. The use of a ligand with strong electron-withdrawing groups is critical for the success of the method.