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Synfacts 2007(4): 0396-0396
DOI: 10.1055/s-2007-968359
DOI: 10.1055/s-2007-968359
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Ring Expansion of Methylenecyclopropane Carboxamides
C. Taillier, M. Lautens*
University of Toronto, Canada
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968359-1.jpg)
Significance
A nice approach for enantioselective ring expansion of monoactivated methylenecyclopropanes has been developed. The use of MgI2 as Lewis acid starting material and CP-IndaBOX as chiral ligand afforded the best results, giving adducts in the range of 49-86% ee. Of the tested imine substrates, electron-withdrawing groups on the aryl ring succeeded in yielding higher selectivities than substrates with strongly electron-donating groups.