Asymmetric Amine-Intercepted Nazarov Cyclization

The chiral auxiliary directed addition of a propargyllithium reagent to a morpholino enamide, followed by exposure of the adduct to activated dry Florisil in the absence of solvent and in the presence of a primary or secondary amine, leads to a cascade of reactions that results in the formation of an aminocyclopentenone as a single diastereoisomer. The reaction can also be conducted intramolecularly.