UROP Proceedings 2022-23

School of Science Department of Chemistry 10 Deep Learning in Synthesis Planning Supervisor: SU, Haibin / CHEM Student: PANG, Chun Pan Terry / SSCI Course: UROP1000, Summer The integration of artificial intelligence and computational software has opened up new possibilities for organic chemists in pursuit of innovative synthetic strategies. This report discusses the development of a software capable of transforming chemical structure images from academic journals into SMILES format, a computer-recognizable language representing chemical structures. SMILES not only provides unique identifiers for chemical compounds but also offer compact representation, which promotes storage and computational efficiency. Our software consists of file handling, segmentation, translation, and output components, enabling efficient and automated chemical information retrieval and standardization. Using OChemR, an open-access algorithm as backbone, molecular recognition and SMILES translation can be achieved. This software addresses the inadequacy of current molecular recognition programs and accelerates the development of meta-heuristic models, such as molecular transformers, by feeding a massive, accurately translated database of organic reactions. While still in the development stage, this software shows potential to advance organic synthesis planning, as well as overall chemical information storage. Development of New Catalytic Organic Processes Supervisor: SUN, Jianwei / CHEM Student: HO, Hang Chi / CHEM-IRE Course: UROP2100, Spring Kinetic resolution represents a powerful strategy for the construction of multiple chiral molecules in one pot. While the asymmetric reactions of ortho- and para- hydroxyl benzylic alcohols and their corresponding quinone methides have been extensively explored, the properties of a meta-hydroxyl group as a directing group in asymmetric organocatalysis is relatively underdeveloped. Herein, we disclose a meta-hydroxyl directed kinetic resolution of biaryl alcohols using sulfur nucleophiles. Green Chemistry in Organic Synthesis Supervisor: TONG, Rongbiao / CHEM Student: MA, Muyang / SSCI Course: UROP1100, Summer Green chemistry is an area which aims to reduce the use of hazardous compounds and maximize the utilization of atoms in the chemical process, and it has been emphasized in recent years. Aryl halides are important intermediates and have been widely used in organic synthesis. Herein, we are going to report a green protocol by using arylboronic acid, oxone and halide salt, which would form C-X bond in situ and just produce a nontoxic byproduct (potassium sulfate), to replace the traditional methods like Sandmeyer reaction and NXS in the halogenation reaction. We also investigate and compare the effect of different substrates and different halogens to screen out the condition for the halogenation reactions.