Synfacts 2007(3): 0281-0281  
DOI: 10.1055/s-2007-968267
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Highly Selective Asymmetric Ring Opening of meso-Epoxides

Contributor(s): Mark Lautens, Praew Thansandote
M. Boudou, C. Ogawa, S. Kobayashi*
The University of Tokyo, Japan
Further Information

Publication History

Publication Date:
20 February 2007 (online)

Significance

A scandium catalyst and a chiral bipyridine ligand were used to perform asymmetric ring openings of meso-epoxides in moderate to good yields and good enantioselectivities. The nucleophiles used to perform this desymmetrization include N-heterocycles, thiols and alcohols. This is an extension of the group’s previous discovery of Lewis acid surfactant combined catalysis (LASC) using only water as solvent (J. Am. Chem. Soc. 2000, 122, 7202-7207).