Novel sulfonylpolystyrene-supported prolinamides as catalysts for enantioselective aldol reaction in water

Five novel prolinamides derived from 1,n-diamines supported on commercially available sulfonylpolystyrene have been synthesized and successfully applied in diastereo- and enantioselective aldol reaction in water or, in one case, neat conditions. Excellent dr and er were obtained by reaction of different cyclohexanone derivatives with aromatic and heteroaromatic aldehydes in the presence of the catalysts and AcOH as co-catalyst. The supported organocatalysts work in low loading (5 mol %) exhibiting similar performances than homogeneous prolinamides, and can be reused, after activation, without loss of activity. (C) 2013 Elsevier Ltd. All rights reserved.