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Synthesis 1992; 1992(6): 558-561
DOI: 10.1055/s-1992-26165
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Palladium(II)-Catalyzed Acetalization of Allylic Acetates and Its Utilization for the Synthesis of 2-Cyanovinyl Ketones

Takahiro Hosokawa* , Shunji Aoki, Shun-Ichi Murahashi
  • *Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560, Japan
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Publication Date:
17 September 2002 (online)

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α-Cyanoallyl acetate (1a), when treated with methanol in the presence of bis(acetonitrile)dichloropalladium(II) catalyst, is acetalized at the terminal olefinic carbon to give 1-cyano-3,3-dimethoxypropyl acetate (2). γ-Substituted α-cyanoallyl acetates give 3-substituted 1-cyano-3-oxo-propyl acetates 5 from which 2-cyanovinyl ketones 11 are obtained in good yields.