News & Events

Enantioselective Synthesis of Hemiaminals via Pd-catalyzed C-N Coupling

Date: 
Thursday, February 28, 2019 - 18:30 to 19:30
Speaker: 
Dr. Qinghao Chen
Affiliation: 
Merck
Event Category: 
ODG - Organic Discussion Group
Location: 
Chemistry D215

Abstract:

Elbasvir and ruzasvir are the NS5A protein inhibitor in Merck’s oral combination therapy for the treatment of hepatitis C. The aminal stereocenter of elbasvir was efficiently constructed by a novel Pd-catalyzed asymmetric intramolecular C-N coupling. This transformation has been shown to be general for a wide variety of N,O- and N,N-acetals. Mechanistic studies revealed the active ligand to be a diphosphine monoxide. This presentation will discuss the discovery, optimization, scope, and mechanstic insights of the asymmetric aminal synthesis.