Synfacts 2011(8): 0865-0865  
DOI: 10.1055/s-0030-1260740
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Epoxidations of Disubstituted Enones with Iron

Contributor(s): Mark Lautens, Stephen G. Newman
Y. Nishikawa, H. Yamamoto*
The University of Chicago, USA
Further Information

Publication History

Publication Date:
20 July 2011 (online)

Significance

Asymmetric epoxidation is a highly investigated field, featuring many diverse catalysts which can react with a broad range of substrates. Despite years of study, the epoxidation of acyclic β,β-disubstituted enones is still a synthetic challenge. These substrates are typically less electrophilic than their monosubstituted derivatives because of their increased steric bulk and lack of conjugation between the alkene and carbonyl group due to steric repulsion. The authors have developed an iron catalyst with novel chiral phenanthroline ligands that allows asymmetric ­epoxidation of these substrates in good yields and enantiomeric excess.