Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination

The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd-2(dba)(3), Xphos, and Cs2CO3 in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.