An Efficient and General Entry to (<i>Z</i>)-<i>α</i>-Fluoro-<i>β</i>-substituted Acrylaldehydes Based on the Coupling Reaction of <i>α</i>-Fluoro-<i>β</i>-amino Acrylaldehydes with Organolithium Reagents

• Kazumasa Funabiki

  Department of Chemistry, Faculty of Engineering, Gifu UniversityYanagido, Gifu

• Takao Kurita

  Department of Chemistry, Faculty of Engineering, Gifu UniversityYanagido, Gifu

• Masaki Matsui

  Department of Chemistry, Faculty of Engineering, Gifu UniversityYanagido, Gifu

• Katsuyoshi Shibata

  Department of Chemistry, Faculty of Engineering, Gifu UniversityYanagido, Gifu

Abstract

α-Fluoro-β-amino acrylaldehydes (2), readily available from the reaction of polyfluoroalkenyl tosylates (1) with dialkylamines in the presence of triethylamine and a catalytic amount (10 mol%) of tetrabutylammonium fluoride (TBAF), reacted smoothly with various organolithium reagents at −78 °C for 0.5 h, followed by hydrolysis with 10% hydrochloric acid at room temperature for 1 h to afford the corresponding (Z)-α-fluoro-β-substituted acrylaldehydes (3) via allylic rearrangement in good to excellent yields.

Journal

• Chemistry Letters

  Chemistry Letters 26 (8), 739-740, 1997-08-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169062813952
• NII Article ID: 10002613671
• NII Book ID: AA00603318
• DOI: 10.1246/cl.1997.739
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/26/8/739/56075479/cl.1997.739.pdf
• Data Source:
  • Crossref
  • CiNii Articles