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Synfacts 2009(8): 0866-0866
DOI: 10.1055/s-0029-1217428
DOI: 10.1055/s-0029-1217428
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Zirconium-Mediated Synthesis of Cyclobutyl Derivatives
E. Tsoglin, H. Chechik, G. Karseboom, N. Chinkov, A. Stanger, I. Marek*
Technion - Israel Institute of Technology, Haifa, Israel
Further Information
Publication History
Publication Date:
23 July 2009 (online)
Significance
The authors described the stereoselective preparation of metalated cyclobutane derivatives through treatment of Z-vinyl carbamate with Et2ZrCp2. The resulting cyclobutyl zirconium reagents reacted with various electrophiles leading only to syn-diastereomers. It is believed that the reaction proceeds through a carbometalative ring expansion followed by an intramolecular migratory insertion.