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Synfacts 2006(8): 0812-0812  
DOI: 10.1055/s-2006-941949
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Methylenecyclopropanes

Contributor(s): Mark Lautens, Yann Béthuel
Z. Yang, X. Xie, J. M. Fox*
University of Delaware, Newark, USA
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Publikationsverlauf

Publikationsdatum:
21. Juli 2006 (online)

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Significance

The enhanced reactivity (strain energy: 40 kcal×mol-1) of methylenecyclopropanes towards various reaction conditions makes them valuable building blocks for the preparation of complex molecules. However, methods for their enantioselective preparation remain limited. In the present paper the synthesis of dia­stereomerically pure methylenecyclopropanes in good to excellent yields is described, starting from enantio­enriched cyclopropenes (for the preparation of chiral cyclopropenes, see: H. M. L. Davies, G. H. Lee Org. Lett. 2004, 6, 1233-1236).