Significant advancements have been made in the field of enantioselective catalysis through the exploration of the unique properties of pyrrolidinyl gold(I) complexes.
A groundbreaking study conducted by Prof. Echavarren’s group at the Institute of Chemical Research of Catalonia (ICIQ-CERCA), in collaboration with Dr. Maria Besora from the URV in Tarragona, has been published in JACS Au. This study utilizes a combination of Density Functional Theory (DFT) calculations and the newly developed NEST App to provide a deeper understanding of electronic and steric effects, ultimately facilitating the design of novel chiral ligands for enantioselective reactions.
Building on their previous work with chiral gold(I) catalysts, the research team focused on investigating the impact of structural modifications on the electronic and steric effects of ligands. Over 20 new gold(I) complexes were synthesized and evaluated in two key reactions: the enantioselective formal [4+2] cycloaddition of arylalkynes with alkenes, and the atroposelective synthesis of 2-arylindoles through the cyclization of sulfonamidyl diarylacetylenes. The novel catalysts exhibited excellent enantioselectivities, showcasing the enormous potential of the pyrrolidinyl gold(I) complex scaffold.
The computational work carried out by Dr. Imma Escofet, in collaboration with Dr. Besora, was instrumental in the development of the innovative open-source tool called NEST App. This software calculates the volume occupied by the atoms of a molecule within a defined capsule-shaped region, enabling a detailed investigation of steric effects within the binding pockets of gold(I) catalysts.
The data generated by the NEST App provided valuable insights and facilitated the prediction of experimental enantioselectivities, showing reasonable agreement with the actual experimental results. This new tool accelerates the process of designing new chiral ligands, significantly reducing optimization time.
This study not only advances our understanding of enantioselective catalysis with pyrrolidinyl gold(I) complexes but also establishes a powerful platform for the development of highly efficient and selective catalysts. These findings have the potential to revolutionize the field and drive transformative advancements in the synthesis of complex chiral molecules.
More information: Giuseppe Zuccarello et al, Enantioselective Catalysis with Pyrrolidinyl Gold(I) Complexes: DFT and NEST Analysis of the Chiral Binding Pocket, JACS Au (2023). DOI: 10.1021/jacsau.3c00159
Citation: Unlocking the potential of enantioselective catalysis: Advancements in pyrrolidinyl gold(I) complexes (2023, June 19) retrieved 19 June 2023 from https://phys.org/news/2023-06-potential-enantioselective-catalysis-advancements-pyrrolidinyl.html
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Shambhu Kumar is a science communicator, making complex scientific topics accessible to all. His articles explore breakthroughs in various scientific disciplines, from space exploration to cutting-edge research.
