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Synfacts 2008(11): 1191-1191  
DOI: 10.1055/s-0028-1083422
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Desymmetrization via Ring Opening of Strained Alkenes

Contributor(s): Mark Lautens, Frédéric Ménard
T. Nishimura*, E. Tsurumaki, T. Kawamoto, X.-X. Guo, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

The desymmetrization of strained alkenes was achieved with excellent enantioselectivity using virtually neutral conditions. The reaction delivers chiral building blocks from a ring opening of meso-azabicycles. The protocol provides an asymmetric alternative to a similar reaction using a Ni catalyst previously reported by Cheng and co-workers (Org. Lett. 2002, 4, 1679). Typically, the starting materials are prepared by a cycloaddition between a benzyne precursor and a protected pyrrole.