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Synfacts 2009(1): 0063-0063  
DOI: 10.1055/s-0028-1087400
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific and Regioselective Ring Expansion of Cyclopropanes

Contributor(s): Mark Lautens, Jane Panteleev
H. Xu, W. Zhang, D. Shu, J. B. Werness, W. Tang*
University of Wisconsin, Madison, USA
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

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Significance

Rearrangement of cyclopropyl ­metal carbenes to cyclobutenes has been well documented in enyne chemistry by the groups of Trost, Echavarren, and Fürstner. The authors report an examination of the scope of this rearrangement in terms of catalysts and substrates, accessing highly substituted cyclobutenes with full retention of stereochemistry. The regioselectivity of the ring expansion is examined in terms of steric and electronic parameters of the substrates and catalyst.

Review: H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charette Chem. Rev. 2008, 103, 977-1050.