Addition reactions of metal enolates of carbonyl compounds to imines, the so-called Mannich-type reaction, represent an important class of carbon-carbon bond-forming reactions. [1] Reflecting the potential utility of the Mannich adducts in the synthesis of nitrogen-containing compounds, [2] we [3] and others [4] have reported efficient methods for catalytic enantioselective Mannich-type reactions. [5] In our previous reports, however, the pre-activation of ketones to form silyl enol ethers was necessary. To meet the present need for atomeconomical processes, the direct addition of pronucleophiles to imines is highly desirable. [6] Recently we reported that chiral Pd complexes 1 and 2 reacted with 1,3-dicarbonyl compounds, such as b-ketoesters, to give chiral Pd enolates (Scheme 1). [7] Using this Pd enolate chemistry, an efficient catalytic enantioselective Michael reaction with enones was developed. [7a] Interestingly, the chiral enolate A derived from 1 underwent the Michael reaction smoothly, whereas the corresponding Pd enolate derived from 2 was completely inactive. These results indicated that the strong protic acid, trifluoromethanesulfonic acid (TfOH), formed concomitantly with the Pd enolate from 1 and activated the enone to act cooperatively with the Pd enolate A, thereby promoting the CÀC bond-forming reaction. Provided that the reactivity of imines is greatly enhanced by protonation, the above-mentioned Pd enolate chemistry would be applicable to the Mannich-type reaction. To our knowledge there has been only one reported example of the use of b-ketoesters in a catalytic asymmetric Mannichtype reaction, where Jørgensen and co-workers [8] achieved excellent enantioselectivities of more than 90 % ee. However, only the imine tested was a highly reactive N-p-toluenesulfonyl-protected imino ester and the scope of the available [*] Dr.