Highly efficient and stereoselective access to (Z)-α,β-difluoroallyl alcohols and (Z)-α-fluoro-α,β-unsaturated aldehydes based on the reaction of 2,3,3-trifluoro-1-propenyl p-chlorobenzenesulfonate with Grignard reagents

✍ Scribed by Kazumasa Funabiki; Yoshitaka Fukushima; Tomomi Inagaki; Eiji Murata; Masaki Matsui; Katsuyoshi Shibata

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 254 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00046-x

✦ Synopsis

2,3,3-Trifluoro-l-pmpenyl p-chlorobenzenesulfonate (1), readily available from 2,2,3,3tetrafluoropmpanol, reacted smoothly with various Grignard reagents at 50 °(3 to afford the corresponding (Z)-a, fl-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed in the presence of a catalytic amount of montmorillonite KI0 (Clay) to provide (Z)-tx-fluoro-tx,fl-unsaturated aldehydes 3 in good yields.