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The \u03b3\u2010nitro\u20102\u2010alkoxycarbonyl pyrrolidines thus obtained in either their <jats:italic>endo<\/jats:italic> or <jats:italic>exo<\/jats:italic> forms were functionalized and coupled to yield the corresponding \u03b3\u2010dipeptides. The catalytic properties of these latter dimers were examined using aldol and conjugate additions as case studies. When aldol reactions were analyzed, an additive behavior in terms of stereocontrol was observed on going from the monomers to the dimers. In contrast, in the case of the conjugate additions between ketones and nitroalkenes, the monomers did not catalyze this reaction, whereas the different \u03b3\u2010dipeptides promoted the formation of the corresponding Michael adducts. Therefore, in this latter case emergent catalytic properties were observed for these novel \u03b3\u2010dipeptides based on unnatural proline derivatives. 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