This diploma thesis deals with the synthesis of chiral five-membered carbacyclic molecules via iminium-enamine activation using chiral secondary amines. The first part of thi diploma thesis describes the synthesis of starting materials for domino Michael addition/α-alkylation reaction, i.e. the synthesis of α,β-unsaturated aldehydes and 1-bromo-3-nitropropane. The second part of this diploma thesis is focused on the optimization of reaction conditions and the application of the domino Michael addition/α-alkylation reaction, that leads to the formation of cyclopentancarbaldehydes with contiguous stereogenic centres. Key words Asymmetric synthesis, organocatalysis, domino reaction, Michael addition, cyclopentanes.