Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives
Xabier del Corte, Adrián López‐Francés, Aitor Maestro, Edorta Martínez de Marigorta, Francisco Palácios, Javier Vicario
Abstract
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.
Topics & Concepts
ChemistryEnamineLactamEnantioselective synthesisCatalysisPhosphoric acidEnolFluorineBrønsted–Lowry acid–base theoryOrganic chemistryPhosphorusCombinatorial chemistryOrganocatalysisOrganophosphorus compounds synthesisFluorine in Organic ChemistryCarbohydrate Chemistry and Synthesis