CAS-Croucher Joint Labs

The CAS-Croucher Funding Scheme for Joint Laboratories is the outcome of an agreement between The Chinese Academy of Sciences (CAS) and the Croucher Foundati...

Asymmetric formation of carbon-carbon bond with catalytic tetrahydroxy-tetraphenylene species & SIOCPhox ligands: application in total synthesis of dhilirolide D & isocedrene family

The Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis aims to develop new SIOCPhox ligands and new tetrahydroxytetraphenylene catalysts for the novel C-C bond formation reactions, and to strengthen research collaboration between Hong Kong and Shanghai chemists.

The development of effective catalysts for organic chemistry, especially for drug discovery and materials science, is of fundamental importance both in basic research and in industrial applications. In view of the importance of ligand designs in developing new catalysts or their precursors for optimizing activity and selectivity, the Joint Laboratory plans to develop a series of new ferrocene-based ligands as well as novel tetrahydroxytetraphenylene-based organocatalysts on the basis of the researchers' previous works. These chiral ligands and relevant organocatalysts will be applied to the total syntheses of structurally complex and biologically significant natural products.

The Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis was established in 1999 as a joint venture between the Chinese University of Hong Kong, The University of Hong Kong, and Shanghai Institute of Organic Chemistry, the Chinese Academy of Sciences (CAS). The main research domains of this Joint Laboratory are

  • chirality and asymmetric catalysis 
  • C–H bond activation 
  • environmental-friendly catalysis methodology 
  • polymer sciences 
  • total synthesis of bioactive naturally occurring molecules

Tetraphenylenes are structurally exceptional molecules with rigid conformations so that substituents of these compounds demonstrate highly directional dispositions. As such, these molecules are potential candidates as organocatalysts or ligands in asymmetric synthesis. The Joint Laboratory aims to conduct further research on the chemistry of hydroxytetraphenylenes, then design and synthesise new SIOCPhox ligands and new tetrahydroxytetraphenylene catalysts with tunable electronic and steric properties.

Palladacycles, as readily available, air- and moisture-tolerant, highly active catalysts, have attracted much attention over the years. The researchers have recently developed a number of benzylic substituted chiral oxazoline ligands and their palladium complexes that show high catalytic activities and enantioselectivites in asymmetric allylic alkylation Heck reactions. The unique structure of these ligands provides an opportunity to develop some novel chiral palladacycles. In order to explore their applications in asymmetric synthesis of a wide range of bicyclic/heterocyclic alkenes, the Joint Laboratory aims to prepare new SIOCPhox ligands and new tetrahydroxytetraphenylene catalysts and examine their catalytic properties and reaction mechanisms.

In addition, the Joint Laboratory plans to develop an enantioselective route towards functionalised bicyclo[3.2.1]octen-2-ones based on their recent total synthesis of pallavicinin family. The team will apply the newly developed C-C bond formation reactions to the total synthesis of dhilirolide D and isocedrene family. These molecules are potentially bioactive and could provide important insights into their structure-activity relationships.

Through these intellectual pursuits, the Joint Laboratory hopes to not only train young researchers, enhance the basic understanding of catalyst design, but also lead to new highly active catalyst systems for green chemical processes, and as a result, shed light on important reaction mechanisms and structure-activity relationships.

Between 2012 and 2015, a total of 38 publications originated from this joint project.
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