Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives.

A Brönsted acid multicomponent reaction between pyruvate derivatives, amines, and aldehydes for the preparation of phosphorus and fluorine substituted γ-lactam derivatives is presented. Depending on the substitution in the resulting 1,5-dihydro-2H-pyrrol-2-one substrates, the reaction provides enol- or enamine-derived γ-lactams. Some enantioselective examples of this reaction are also reported using chiral phosphoric acids as organocatalysts. Moreover, several synthetic applications of γ-lactam derivatives are presented including some examples of highly diastereoselective transformations.