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Synfacts 2010(12): 1373-1373  
DOI: 10.1055/s-0030-1258888
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Cyclopropanation Using Dimethyl Diazomalonate

Contributor(s): Mark Lautens, Stephen G. Newman
T. Nishimura*, Y. Maeda, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

Many well-developed dirhodium(II) carboxamidates and carboxylates exist for highly enantioselective cyclopropanations of alkenes with diazo compounds (see Review below). Due to often low reactivity and enantioselectivity no highly asymmetric cyclopropanation using diazo­malonates exists. The authors discovered that chiral cyclopropane gem-diesters can be prepared in good yields and enantioselectivies by ­using a cationic chiral rhodium-diene complex.

Review: H. Pellissier Tetrahedron 2008, 64, 7041-7095.