Malcolmson Lab Develops Catalytic Three Component Regiodivergent Reactions to Prepare Allylic Alkyl Amines

Three-component couplings proceed with alkenyl triflates and several amines

The Malcolmson lab has developed a three component carboamination of dienes utilizing aliphatic and aryl amines in conjunction with alkenyl electrophiles. Two different Pd-based catalysts allow for regiodivergent introduction of the amine reagent. The multicomponent coupling, together with the regiodivergence, enables the rapid production of a library of small molecule building blocks to facilitate drug discovery. Mechanistic experiments suggest the origin of regioselectivity with both catalysts, including a key pi-stacking organization of the transition state with phosphoramidite ligand L5. Read more about this methodology in The Journal of the American Chemical Society.