Abstract by Tanner Brinley
Chemistry and Biochemistry
Pyrroloindolines made by Reisman’s synthesis have shown anti-cancer characteristics and are made through the 3+2 cycloaddition of 2-amidoacrylate and an indole, via a chiral ligand for stereoselectivity. This method however gives low yield and limited stereoselectivity. Our overall goal is to create multiple pyrroloindoline products using our 3+2 cycloaddition reaction. These products can be used in a variety of healthcare capacities including cancer and disease treatment. We have proposed two pathways to create a pyrroloindoline through 3+2 cycloaddition of N-methyl-3-methyl indole and acyloxazolidinone. 1) using a chiral auxiliary. 2) mirroring the Reisman reaction using a chiral ligand and an achiral oxazolidinone. We hypothesize that acyloxazolidinone with a chiral auxiliary group will create stereoselective reactions which will stop a mixture of enantiomers from forming during the 3+2 cycloaddition. We believe the benzyl group hinders the approach of the substrate on one face giving us only diastereomers and easier separation.