Chiral Vicinal Diamines

Mingkang Zhou: I am the developer of diboron chemistry, and under the guidance of predecessors, I have developed the reductive coupling of aldimines and ketimines.

Lung Wa Chung: I am involved in the computational chemistry part, which helps our teams to understand the reaction mechanism and origin of stereoselectivity.

Xiao-Xuan Chen: My role within the team was focused on theoretical computational research. I contributed to understanding the underlying principles and mechanism through systematic DFT studies, providing the insights on uncovering the factors responsible for the excellent enantioselectivity observed in the synthesis of chiral vicinal tetrasubsubstituted diamines.

Qinghai Zhou: Part of computational work. Under the supervision of Professor Chung, calculating the stereoselectivity of reductive coupling of isoquinolines templated by chiral diborons.

Guangqing Xu: Discovered the reductive coupling of isoquinoline templated by bis(pinacolato)diboron, and developed the general systems of reductive coupling of imines.

Mingkang Zhou: How to obtain a stable and high-purity dialdimine starting material has become the greatest challenge. How to obtain a stable and high-purity dialimine starting material has become the greatest challenge.

Lung Wa Chung: Achieving high stereoselectivity to form vicinal tetrasubstituted diamines is very challenging synthetically. The Tang group developed a series of new and functionalised chiral diborons to attain such a goal. Meanwhile, these functionalized chiral diborons can adopt many possible conformations, which poses a challenge for our computational study in order to understand the origin of the stereoselectivity at an atomic resolution.

Kaidi Li: From my perspective, upon recognising the great potential of this approach, we became eager to know its practicality for large-scale synthesis. The original process, commencing from S-Mandelic acid, led to unsatisfactory results, limiting the scope of elaboration and application. After months of efforts, the team moved to a protected mandelic ester, which brought the opportunity for a green and efficient chiral diboron synthesis.

Xiao-Xuan Chen: This research is groundbreaking due to its introduction of a novel asymmetric synthesis method for vicinal tetrasubstituted diamines, achieving remarkable enantioselectivity and yields, paving the way for diverse applications in creating therapeutic agents and bioactive molecules, and advancing catalysis through the innovative use of chiral diborons, thereby opening up new avenues in chemical reaction processes.

Guangqing Xu: This work was not only valuable for synthetic organic chemistry but also made a breakthrough for pericyclic reaction theory.

Kaidi Li: Over centuries, chemists have utilised chiral amines for the development of biologically active small molecules and the synthesis of chiral ligands, necessitating a general and efficient approach to generate diverse libraries. This chemistry paves the way in this direction, streamlining processes and simplifying endeavours.

Mingkang Zhou: It provides a brand-new chiral source and a recyclable synthesis strategy, making the synthesis of chiral diamine-derived catalysts and ligands highly efficient and convenient.

Guangqing Xu: The development of this project provides a practical and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines. This will significantly facilitate the chemistry of chiral vicinal diamines as ligands and building blocks for pharmaceutical and fine chemistry.

Xiao-Xuan Chen: Collaboration in the chemical sciences is vital for fostering interdisciplinary research, accelerating innovation, and solving complex problems by combining diverse expertise and resources. It’s the cornerstone of scientific advancement and breakthrough discoveries.

Wenjun Tang: Collaboration makes the impossible a wonder.

Dongping Chen: Freedom, encouragement, support.

Lung Wa Chung: Critical and open-minded thinking; encouraged to overcome challenges; solving problems in unique ways; cross-disciplinary collaboration.

Wenjun Tang: A good research culture should be collaborative, inspiring, communicative, hardworking, and productive.