Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies
Third-party funded project
Project title Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies
Principal Investigator(s) Sparr, Christof
Organisation / Research unit Departement Chemie / Organische Chemie (Sparr)
Project start 01.10.2014
Probable end 30.09.2017
Status Completed
Abstract

The configuration of axially chiral compounds fully governs the biological activity of important pharmaceutical entities and is completely translated from atropisomeric ligands to high-value products in numerous remarkably efficient catalytic processes. However, atroposelective catalysis remained a niche area in the vast field of asymmetric synthesis. This underrepresentation offers intriguing opportunities for the development of novel synthetic methods and strategies. Inspired by the aromatic polyketide biosynthesis, the proposed method takes advantage of an aromatization as ample driving force and utilizes efficient transfer of central to axial chirality from the catalyst to the product. Readily available substrates will be treated with secondary amine organocatalysts to initiate a cyclization event, inducing an aromatization process to selectively form the desired atropisomer after release of the catalyst.

Keywords catalysis, rapid generation of molecular complexity, environmentally benign chemistry, reaction cascades, reaction mechanisms
Financed by Swiss National Science Foundation (SNSF)
   

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