Research Projects

This research project aims to design and synthesise novel piperidine tethered dienal, and aminocatalytic construction of stereocenters via in situ generated hetero ortho-quinone dimethide (HoQDM) to more remote positions from the stereo-differentiating element than described up to date. As of late, Melchiorre and coworkers introduced the remote [4+2]-annulation of in situ formed hetero ortho-quinonedimethides generated in situ from indole tethered dienal through trienamine catalysis. In 2022, our group disclosed the synthesis and applications of novel pyrrolidine tethered dienal in [4+2]-annulation reaction through in situ formed HoQDM intermediate. The current proposal wishes to put another step forward by exploring the reactivity of in situ-produced hetero ortho-quinone dimethide (HoQDM-tetraenamines/trienamines) from piperidine tethered dienal and trienals outfitted amino-catalyst at seven to eight bonds away from the stereo relay. If successful, this will allow for enantioselective functionalization at an even more remote (eighth) position and permit access to a tremendous cluster of modern tandem and other multicomponent reactions through remote 4+2 annulation. Eventually, this project should provide a premise for the evolution of one-pot strategies appropriate to synthesising lycopodium natural products analogues (octa and decahydroquinoline cores). To attain this objective, the scope and restrictions of this novel actuation mode will be examined with an array of piperidine tethered enals/dienals and electrophiles. Common aminocatalysts will be explored, but the sketch, synthesis, DFT studies and anti-Alzheimer’s screening of all the perhydroquinoline scaffolds obtained through this protocol will be an important portion of this project.