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

  • Ikuzo Nishiguchi
Conference paper

Abstract

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.

Keywords

Acid Chloride Acetic Anhydride Acid Anhydride Aliphatic Aldehyde Undivided Cell 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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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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