In the first part of this talk, different expansion reactions, like the synthesis of dibenzoxepines and dibenzazepines with diazomethane reagents, will be shown. Next, I will present an approach for the asymmetric synthesis of tricyclic compounds, via desymmetrization of cyclohexadienones under aminocatalytic conditions. At the end of this communication, the use of bifunctional catalytic systems for the activation of silyl-dienol ethers for the synthesis of Rauhut-Currier type products will be presented. The process takes place under smooth conditions, non-anionic conditions, and with a high enantiomeric excess. A rational mechanistic pathway is presented based on DFT and mechanistic experiments.