GTR ORGANIC SEMINAR
この度、ACP Lectureship 2025を受賞された南方科学技術大学（SUSTech）の新進気鋭な若手研究者Zhe Dong先生を招聘し、10 月 26 日(月) 16:30からVBL 3F、ベンチャーホールにて講演会を開催します。この機会に是非ご参加ください。
四面体型の不斉中心が、反応性の高い平面型カルボカチオンや炭素中心ラジカルへと変換される際には、しばしば立体化学情報が失われます。Dong先生は、このようなカチオン、ラジカル、および有機金属反応過程を通じて、立体化学情報を保持、伝達、あるいは再構築するための相補的な手法について研究しておられます。本セミナーでは、組織化されたイオン対、協奏的な骨格再編成、分子内置換反応、そして立体配置を保持するラジカルという相補的な戦略を通じて、反応性の高い中間体が関与する反応においても、立体化学情報を保持し、それを積極的に活用する方法について講演されるものと思います。
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.
お問い合わせ：Muhammet Uyanik &石原一彰（内線 3206，3331）
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登録締め切り：10月22日