The α-chiral tetrahydroquinoline (THQ) motif is an important structural construct found at the core of a myriad of natural products and biologically active molecules. Alkynylation of pyridines at the α-position to nitrogen would afford chiral 1,2-dihydropyridines containing multiple synthetic handles allowing for elaboration to highly substituted THQ compounds. We have previously reported on atropisomeric biaryl P,N-ligands that have been demonstrated to catalyze alkyne addition reactions to a variety of electrophiles with high enantioselectivities. Encouraged by these results, we envisioned an enantioselective Cu-catalyzed nucleophilic dearomatization of pyridines. The development of this methodology and its application will be presented.

Catalytic enantio- and regioselective alkynylation of pyridines

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.