Design and synthesis of a stereodynamic catalyst with reversal of selectivity by enantioselective self‐inhibition

Scholtes, Jan Felix and Trapp, Oliver (December 2019): Design and synthesis of a stereodynamic catalyst with reversal of selectivity by enantioselective self‐inhibition. In: Chirality, Vol. 31, No. 12: pp. 1028-1042

Abstract

Chirality plays a pivotal role in an uncountable number of biological processes, and nature has developed intriguing mechanisms to maintain this state of enantiopurity. The strive for a deeper understanding of the different elements that constitute such self‐sustaining systems on a molecular level has sparked great interest in the studies of autoinductive and amplifying enantioselective reactions. The design of these reactions remains highly challenging; however, the development of generally applicable principles promises to have a considerable impact on research of catalyst design and other adjacent fields in the future. Here, we report the realization of an autoinductive, enantioselective self‐inhibiting hydrogenation reaction. Development of a stereodynamic catalyst with chiral sensing abilities allowed for a chiral reaction product to interact with the catalyst and change its selectivity in order to suppress its formation, which caused a reversal of selectivity over time.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0899-0042
• Language: English