Synfacts 2009(8): 0866-0866  
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

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
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.