Remarkable reversal of stereoselectivity in Wittig-type olefinations of α-fluorinated alkyl aryl ketones

Article abstract of DOI:10.1016/S0040-4039(00)61141-3

Remarkable reactivity and reversal of stereoselectivity in the Wittig-type olefinations of α-fluorinated alkyl aryl ketones were described. Stabilized Wittig and Horner-Emmons reagents with these ketones selectively afforded the olefinic products in the stereochemically opposite fashion to the non-fluorinated ketone cases. The Still's reagent further reversed the stereochemical outcome with the fluorinated ketones.