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The pyrrolidine scaffold is undoubtedly a privileged motif in asymmetric aminocatalysis. Pyrrolidine-based organocatalysts are often able to promote efficient carbon–carbon and carbon–heteroatom bond-forming reactions, via both enamine or iminium-ion, almost always with outstanding levels of stereocontrol. In the last fifteen years a huge number of structural modifications have been proposed on the pyrrolidine ring, with the aim to obtain chiral organocatalysts possessing enhanced activity and different patterns of reactivity. In this chapter less-common pyrrolidine-based organocatalysts will be presented and their application in asymmetric transformation will be discussed and analysed.

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