Highly chemoselective formation of aldehyde enamines under very mild reaction conditions.
Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.
Bélanger
Guillaume
G
Laboratoire de Synthèse Organique et de Développement de Stratégies de Synthèse, Département de Chimie, Université de Sherbrooke, 2500 boulevard Université, Sherbrooke, Québec, J1K 2R1, Canada. guillaume.belanger@USherbrooke.ca
Doré
Michaël
M
Ménard
Frédéric
F
Darsigny
Véronique
V