Bridged heterocycles have emerged as important building blocks in drug discovery, as the rigid conformation can help increase potency and target selectivity. Many top selling drugs contain bridged heterocyclic systems, including Chantix�, Spiriva� and Combivent�. Despite the utility and widespread use of these compounds, there are only a few syntheses of bridged heterocycles in the literature, and they typically require extended syntheses and suffer from low product yields. A bis-allylic imidate, formed in two steps from readily available starting materials, can undergo an iridium catalyzed  bis-allylic amination, followed by a ring closing metathesis, resulting in the efficient formation of the desired bridged heterocyclic products. Current work is focused on the use of chiral amines and imidates to form enantioenriched products. Further functionalization of the alkene moiety using chiral catalysis, such as hydroarylation and carbonylation reactions, will lead to functionally diverse, enantioenriched bridged heterocycles.

Formation of bridged heterocycles through a bis-amination/RCM sequence and stereoselective functionalization using asymmetric catalysis

245th National Meeting (2013)

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