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Two novel bifunctional primary amine catalysts 1RA,S,S and 2RA,R,R, which bear both central and axial chiral elements, have been developed to promote highly diastereoselective and enantioselective aldol reactions of arylaldehydes with cyclic and acyclic ketones in the presence of water at room temperature. The catalyst 2RA,R,R afforded the desired products with high levels of antidiastereoselectivity up to 99:1 and enantioselectivity up to 98%, showing that the two chiral elements of catalyst 2RA,R,R are matched, and enhance the stereochemical control. In addition, the catalyst 2RA,R,R was found to catalyze the direct aldol reaction of 4nitrobenzaldehyde with 2cyclohexanone under neat reaction conditions at room temperature with the high antidiastereoselectivity 98:2 and enantioselectivity 98%.