Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts

New trifunctional organocatalysts with a NHTs Bronsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions. The cooperativity between the counterion and the NHTs Bronsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement. Better enantioselectivity was observed for aza-MBH reactions at relatively low catalyst loading (2-5 mol%) under facile conditions. (C) 2010 Elsevier Ltd. All rights reserved.