Asymmetric Carbon-Carbon and Carbon-Silicon Bond Formation of Activated Olefins Promoted by Mg-Metal and Electroreduction

  • Ikuzo Nishiguchi
Conference paper


It has been found in this study that Mg-promoted electron transfer reaction in DMF / trimethylsilyl chloride (TMSC1), and electroreduction using reactive metal anodes of aromatic α, β-unsaturated systems in the presence of aldehydes, TMSCl, and acid chlorides (or acid anhydrides) brought about efficient and selective reductive cross-coupling reactions to give the corresponding γ-butyrolactones, β-silylated and β-acylated products in good yields, respectively. Furthermore, some diastereoselectivity (40–50%) was observed in the β-silylation and β-acylation using chiral α, β-unsaturated amides as the substrates.


Acid Chloride Acetic Anhydride Acid Anhydride Aliphatic Aldehyde Undivided Cell 


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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Ikuzo Nishiguchi
    • 1
  1. 1.Nagaoka University of TechnologyNagaoka, NiigataJapan

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