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Synfacts 2009(8): 0874-0874  
DOI: 10.1055/s-0029-1217436
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Lanthanum(III)-Catalyzed Cyclopropanation

Contributor(s): Mark Lautens, Jacki Kitching
D. J. Hardee, T. H. Lambert*
Columbia University, New York, USA
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Publikationsverlauf

Publikationsdatum:
23. Juli 2009 (online)

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Significance

A lanthanum(III) triflate catalyzed cyclopropanation protocol involving the methylene transfer from epoxides to olefins is described. The resulting aldehydes and ketones are obtained in good yield and the reactions proceed with high ­diastereoselectivity. Furthermore, enantioenriched cyclopropanes can be obtained following asymmetric epoxidation and methylene transfer reactions.