GTR ORGANIC SEMINAR
Date: Oct.26 (Mon), 2026,16:30-18:00
Venue: The Venture Hall, 3F, VBL
Speaker: Assoc. Professor Zhe Dong (Dep.of Chem.,South University of Science and Technology)
Title: Enantiospecific reaction involving highly reactive intermediates
Abstract
Stereochemical information is often lost when a tetrahedral stereogenic center is converted into a highly reactive planar carbocation or carbon-centered radical. This seminar will describe complementary approaches that preserve, relay, or re-establish stereochemical information across cationic, radical, and organometallic reaction manifolds. First, electronically tuned 2-pyridyl ethers transform chiral tertiary alcohols into organized Lewis acid-bound ion pairs that react with trialkylaluminium reagents before racemization. The resulting stereoretentive bimolecular substitution provides direct access to all-carbon quaternary stereocenters from diverse tertiary alcohols. We will then discuss two complementary zinc-enabled reactions of chiral epoxides with boron-stabilized carbanions. In a triatropic rearrangement, a concerted reorganization of three sigma bonds converts epoxides into ring-contracted and skeletally reshuffled products with programmable stereocontrol, enabling a formal [4+2-1] strategy for complex cyclopentane synthesis. Under a related boron-to-zinc transmetalation manifold, an enantiospecific Homo-Boron-Wittig reaction converts chiral epoxides directly into densely substituted cyclopropyl boronic esters through stereoinvertive intramolecular substitution. Finally, we will show that radical stereochemistry need not be synonymous with racemization. Chiral organogermanium precursors generate freely diffusing, configurationally persistent pyramidal germyl radicals that add to activated and unactivated alkenes and participate in nickel/photoredox arylation with high stereoretention. Comparative carbon/silicon/germanium studies reveal why germanium occupies a unique kinetic window in which radical generation and bond formation outcompete rearrangement and pyramidal inversion. Together, these studies establish complementary strategies--organized ion pairs, concerted skeletal rearrangements, intramolecular substitution, and configurationally persistent radicals--for preserving and exploiting stereochemical information in reactions involving highly reactive intermediates.
Biography
Zhe Dong is an Associate Professor in the Department of Chemistry at Southern University of Science and Technology (SUSTech). He received his B.S. in chemistry from Peking University in 2012, where he worked with Prof. Zhi-Xiang Yu. He began his graduate studies at the University of Texas at Austin and earned his Ph.D. from the University of Chicago in 2018 under the supervision of Prof. Guangbin Dong. From 2018 to 2021, he conducted postdoctoral research with Prof. David W. C. MacMillan at Princeton University. He joined the faculty of SUSTech in 2021. His research focuses on developing new synthetic reactions that control stereochemistry across highly reactive intermediates, main-group redox catalysis, and chemical methods for proximity labelling and spatial proteomics. His group has reported advances in stereoselective skeletal editing, enantiospecific transformations of epoxides and tertiary alcohol derivatives, and stereoretentive radical chemistry. His work has appeared in Science, Nature, Nature Chemistry, Nature Catalysis, Nature Communications, and the Journal of the American Chemical Society. His honors include the Yang Cao-Lan-Xian Best Thesis Award, the Chem-Reaxys Symposium Honorary Lectureship, and the Asian Core Program Lectureship Award.
Representative Publications
1. Enantiospecific Homo-Boron-Wittig Reaction: Direct Conversion of Chiral Epoxides to Cyclopropanes.
Lei Tao, Yuan Niu, Yu Chen, Zeen Yan, Ke Wang, Liu Leo Liu, Peiyuan Yu*, and Zhe Dong*. J. Am. Chem. Soc. 2026, 148, 27282-27293.
2. Ligand-Modulated Metal-Radical Polarity Match Enables General 1,2-Dicarbofunctionalization of Ethylene.
Zhexuan Lei, Chu Wang, Anwei Wang, Tao Liu, Zhe Dong*, Weigang Zhang*, and Jie Wu*. Nat. Chem. 2026, advance online publication. doi: 10.1038/s41557-026-02177-8.
3. Leveraging Triatropic Rearrangements for Stereoselective Skeletal Reshuffling.
Yuan Niu, Yu Chen, Meng Zhou, Huihui Zeng, Ke Wang, Peiyuan Yu*, and Zhe Dong*. Science 2026, 391, 171-178.
4. Copper-Catalysed Asymmetric Cross-Coupling Reactions Tolerant of Highly Reactive Radicals.
Li-Wen Fan, Jun-Bin Tang, Li-Lei Wang, Zeng Gao, Ji-Ren Liu, Yu-Shuai Zhang, Dai-Lei Yuan, Li Qin, Yu Tian, Zhi-Chao Chen, Fu Liu, Jin-Min Xiang, Pei-Jie Huang, Wei-Long Liu, Chen-Yu Xiao, Cheng Luan, Zhong-Liang Li, Xin Hong*, Zhe Dong*, Qiang-Shuai Gu*, and Xin-Yuan Liu*. Nat. Chem. 2026, 18, 142-151.
Host: Muhammet Uyanik & Kazuaki Ishihara（Ex:3206,3331）
★GTR international students only
This seminar is "GTR Lecture series on multidisciplinary problems (1pt)".
Enroll in gtr e-portfolio (Dead line: Oct.22nd）．Grades will be judged by report. Report submission from TACT by Nov.9th.