Yes, I think the henry reaction would work with 4-TFM-2,5-DMBA, at leas with a little tweaking of the reaction conditions. If the failure with 4-TFM-BA is due to the strong electron-withdrawing effects of the CF3 group, this should be outweighed by the two methoxy groups, and if ethylenediammonium diacetate (EDDA) fails, just try another catalyst. EDDA fails with piperonal too, but cyclohexylamine and NaOH works for it.
http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)