This article has been reviewed according to Science X's editorial process and policies. Editors have highlighted the following attributes while ensuring the content's credibility: Do Hyun Ryu's research team in the Department of Chemistry at Sungkyunkwan University (SKKU) has developed two new asymmetric catalytic methods for the precise synthesis of complex molecules using chiral organic catalysts. The team demonstrated that a single catalyst can promote two different carbon-carbon bond-forming reactions with high selectivity.
They also developed a method to selectively construct complex ring structures with multiple stereocenters from simple starting materials. Both studies were published in Angewandte Chemie International Edition. The selective synthesis of molecules with the desired structure is important for producing complex molecules such as pharmaceuticals and natural products.
In particular, precisely controlling where a reaction occurs and how atoms are arranged in three-dimensional space is essential because these structural features can determine a molecule's properties and functions. However, controlling multiple reaction sites and stereocenters at the same time remains a major challenge in organic synthesis. In the first study, conducted in collaboration with Hyunwoo Kim's research team at the Korea Advanced Institute of Science and Technology (KAIST), the researchers developed a unified catalytic platform that uses a chiral organic catalyst to achieve two different asymmetric carbon-carbon bond-forming reactions with high selectivity.
The team successfully achieved a highly selective asymmetric allylation reaction that had previously been difficult to control and applied the same catalyst to another carbon-carbon bond-forming reaction, the aldol reaction. A key feature of this study is that one catalyst can precisely control two different reactions. The catalyst selectively activates the desired reaction site while also controlling the three-dimensional structure of the resulting molecules, allowing various chiral compounds to be synthesized with high selectivity.
The products could be further converted into a range of useful molecules and were successfully applied to the synthesis of biologically active natural products, including (+)-dimethyl citramalate. Density functional theory (DFT) calculations also revealed how the catalyst controls both the reaction site and the three-dimensional structure of the products. In the second study, the research team developed a new catalytic reaction for the highly stereoselective synthesis of tetrahydrofuran ring structures from simple starting materials.
Tetrahydrofuran is a five-membered ring containing one oxygen atom and is an important structural framework found in many biologically active natural products and pharmaceuticals. Previously, the synthesis of such complex three-dimensional structures often required starting materials that already contained a specific stereochemical structure. The research team overcame this limitation by using a chiral organic catalyst to construct multiple stereocenters from simple starting materials without pre-existing stereocenters.
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