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Synfacts 2005(3): 0316-0316  
DOI: 10.1055/s-2005-921639
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Ring Opening of meso-Epoxides in Water

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Azoulay, K. Manabe, S. Kobayashi*
University of Tokyo, Japan
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The use of a chiral scandium bipyridine complex (1 mol%) was shown to give high enantioselectivities for the opening of meso-epoxides with water as the sole solvent. The use of scandium tris(dodecyl sulfate) as the scandium source was found to give much better yield and enantioselectivity than scandium triflate. Various anilines and their derivatives were shown to give consistently good results with cis-stilbene as the epoxide substrate. Highest enantioselectivities were obtained for 1,2-bisaryl epoxides.