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Synfacts 2008(2): 0160-0160
DOI: 10.1055/s-2007-992483
DOI: 10.1055/s-2007-992483
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Lanthanum-Catalyzed Asymmetric Cyclopropanation
H. Kakei, T. Sone, Y. Sohtome, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2008 (online)
Significance
The authors describe a catalytic asymmetric Corey-Chaykovsky cyclopropanation of enones with dimethyloxosulfonium methylide. The catalytic system is a lanthanum complex with lithium atoms and chiral BINOL-type ligands. The scope is broad and trans adducts are the sole isomers obtained in all cases. In a competition between double bonds of varying electronic properties, the reaction is highly chemoselective for the more electron-deficient olefin.