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Synfacts 2011(2): 0187-0187  
DOI: 10.1055/s-0030-1259268
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogen Bond Assisted Asymmetric Metal Catalysis

Contributor(s): Hisashi Yamamoto, Zhi Li
P. Fackler, C. Berthold, F. Voss, T. Bach*
Technische Universität München, Garching, Germany
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

By introducing a chiral hydrogen bond connector to an achiral ruthenium-porphyrin complex, asymmetric epoxidation is achieved with substrates that are able to plug to the connector in a controlled orientation. The reaction is highly regio- and enantioselective, because the hydrogen bond linkage is so rigid that the reaction only takes place at the proximal face of the double bond closer to the metal center.