报告题目：Accessing Molecular Complexity and Functionality by Breaking Symmetry of Active Methylene Derivatives

报告人：黄重行（香港大学助理教授）

报告时间：2024年6月17日（星期一）下午16:20-17:10

报告地点：国际校区C3-C204

主办单位：前沿软物质学院、华南软物质科学与技术高等研究院

邀请人：吴钊教授

报告摘要:

　　Active methylene compounds represent a prominent family of structures that are easily available and can provide rapid access to complex molecules. When doubly substituted, these compounds can be rapidly converted to valuable tetrasubstituted stereocenters via asymmetric transformations. Here, we report a prolinol- or pipecolinol-derived tetradentate ligand scaffold that can house two zinc centers or a single magnesium atom to desymmetrize malonic esters and 1,3-diketones. The reductive desymmetrization of disubstituted malonic ester via hydrosilylation has enabled the stereoselective synthesis of various enantioenriched building blocks, including quaternary stereocenters, tertiary alkyl halides, α-tertiary amines, and tertiary alcohols. Consequently, novel and expeditious approaches to bioactive natural metabolites, such as 2-dechlorohalomon, conagenin, and yezo’otogirins, were devised. Meanwhile, the magnesium-catalyzed desymmetric cyanosilylation of acyclic 1,3-diketones using the same ligand scaffolds afforded two vicinal tetrasubstituted carbons. The polyfunctionalized nature of the chiral cyanohydrin products can be used to access molecules of higher complexity, particularly those with consecutive stereocenters.

报告人简介:

　　黄重行博士在2012年于北京大学获得学士学位，师从王剑波教授和张艳教授。随后先后在德克萨斯大学奥斯丁分校以及芝加哥大学董广彬教授课题组学习，并于2017年获得博士学位。于2017至2019年间，在斯坦福大学Barry M. Trost教授课题组从事博士后研究。在2019年，黄重行博士加入香港大学化学系，担任助理教授、博士生导师。其主要研究方向为活泼亚甲基衍生物的不对称转化。