Synfacts 2010(1): 0058-0058  
DOI: 10.1055/s-0029-1218472
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Cyclobutenes with All-Carbon Quaternary Stereocenters

Contributor(s): Mark Lautens, Stephen G. Newman
A. Masarwa, A. Fürstner, I. Marek*
Technion-Israel Institute of Technology, Haifa, Israel, and Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

The synthesis of enantioenriched molecules with all-carbon quaternary stereocenters is exceedingly difficult. The authors use a previously developed transition-metal-catalyzed ring expansion of chiral alkylidenecyclopropanes to access cyclobutenes with high regioselectivity and no loss in enantiopurity.