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

Article abstract of DOI:10.1016/S0040-4039(98)00046-X

2,3,3-Trifluoro-1-propenyl p=chlorobenzenesulfonate (1), readily available from 2,2,3,3-tetrafluoropropanol, reacted smoothly with various Grignard reagents at 50 °C to afford the corresponding (Z)- α,β-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed in the presence of a catalytic amount of montmorillonite K10 (Clay) to provide (Z)-α-fluoro-α,β- unsaturated aldehydes 3 in good yields.