Synfacts 2007(7): 0717-0717  
DOI: 10.1055/s-2007-968668
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Titanium-Mediated Cyclopropanation of Esters with Grignard Reagents

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
O. G. Kulinkovich*, D. G. Kananovich
Belarusian State University, Minsk, Belarus
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

The authors report an optimized protocol for the preparation of cis-1,2-dialkylcyclopropanols. While cis and trans cyclopropanols of type 2a,b are chromatographically separable, the previous procedure gave significant amounts of secondary alcohol of type 3 which could not be separated from the cis product. The authors found that by addition of MeMgI, the yields of cyclopropanols could be increased and the production of secondary alcohol suppressed.