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Synfacts 2010(10): 1162-1162  
DOI: 10.1055/s-0030-1258645
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Cyclopropanation at ppm Catalyst Loading

Contributor(s): Mark Lautens, Stephen G. Newman
P. Pelphrey, J. Hansen, H. M. L. Davies*
University at Buffalo, The State University of New York and Emory University, Atlanta, USA
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

The use of transition metals as ­catalysts allows for many remarkable reactions to take place, which would be impossible in their absence. A major drawback is the high cost associated with many of these precious metals and their associated ligands. As such, achieving high turnover numbers (TONs) is a primary focus in catalysis. The authors present a highly efficient protocol for rhodium-catalyzed, enantioselective cyclopropanations. The use of donor/acceptor carbenoids under solvent-free conditions allows TONs of >1,000,000 to be obtained.