Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and Acrolein

AbstractThe [3+2]-cycloaddition reaction between acrolein and in situ generated acyclic azomethine ylides promoted by a chiral secondary amine to generate C-3 unsubstituted pyrrolidines has been studied in detail. Optimum conditions involve the use of the cheap and readily available l-Proline as catalyst to afford the pyrrolidine cycloadduct with complete diastereomeric control and up to 80% enantiomeric control.