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Synfacts 2010(5): 0556-0556  
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

Contributor(s): Hisashi Yamamoto, Patrick B. Brady
M. Brichacek, L. A. Batory, J. T. Njardarson*
Cornell University, Ithaca, USA
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Publication History

Publication Date:
22 April 2010 (online)

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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.