Enantioselective Functionalizations of alpha-, beta-Unsaturated Carboxylic Acids using Chiral Boronic Acids

• Applicant: Dr. Moritz Balkenhohl
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2019 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 436477447

The enantioselective functionalization of olefins plays a highly important role in modern organic synthesis. So far, a wide variety of asymmetric alkene functionalizations have been reported, with new publications appearing weekly on this very active research field. However, the use of α,β-unsaturated carboxylic acids in alkene transformations remains rather undisclosed and only selected reactions, such as hydrogenations or cycloadditions, are known.Herein it is proposed, that the use of a chiral boronic acid may pave the way for the enantioselective functionalization of α,β-unsaturated carboxylic acids. The carboxylic acid together with the boronic acid should form a boronate intermediate, which may be susceptible towards several transformations, which would allow the asymmetric preparation of a wide range of functionalized carboxylic acids. The project will close the gap in the current state of olefin functionalization and lead to the development of methodologies towards the preparation of chiral carboxylic acids, which are present in a large number of pharmaceuticals and natural products.

• DFG Programme: Research Fellowships
• International Connection: Switzerland
• Host: Professor Dr. Erick M. Carreira