杨晓瑜

杨晓瑜课题组介绍

课题组长 PI 丨研究介绍 Research 丨发表论文 Publication丨组内活动 Group Activities 丨本组成员 Group Menbers 丨往届成员 Alumni

杨晓瑜 Xiaoyu Yang，副教授、研究员（Associate Professor, PI）
通讯地址：物质学院3号楼410A （SPTS 3-410A）
电子邮件：yangxy1@@shanghaitech.edu.cn
ORCID： https://orcid.org/0000-0002-0756-0671 课题组主页： https://www.x-mol.com/groups/Yang_Xiaoyu

2003-2007年，南京大学化学化工学院，学士（导师蒋锡群教授）Nanjing University，BS （with Prof. Xiqun Jiang）

2007-2012年，中科院上海有机化学研究所，博士（导师俞飚研究员） Shanghai Institute of Organic Chemistry, PhD （with Prof. Biao Yu）

2013年至2016年，美国加州大学伯克利分校，博士后（导师Dean Toste教授） University of California, Berkeley, Postdoc (with Prof. Dean Toste)

2016年6月-2022年，上海科技大学物质科学与技术学院，助理教授、研究员 ShanghaiTech University, Assistant Professor, PI

2023年-至今，上海科技大学物质科学与技术学院，副教授、研究员 2022-， ShanghaiTech University, Associate Professor, PI

所获荣誉：2012 上海市优秀毕业生；2012 Reaxy Prize Finalist；2017“浦江人才计划”；2020 Thieme Chemistry Journal Award; 2022 国家优秀青年基金获得者; 2023年浦东新区明珠计划菁英人才

教授课程：有机化学基础（本科生），手性合成（研究生）

研究介绍 (Research Interest)

本课题组主要开展有机合成方法学的研究，利用催化的方法实现有机反应选择性的控制，具体研究方向包括：

1）有机催化的对映选择性反应（Asymmetric Organocatalysis）

不对称有机催化利用不含金属的有机小分子作为催化剂实现不对称反应，相比于过渡金属催化具有催化剂绿色可持续、价格便宜、反应条件温和等一系列优点，是近年来不对称催化领域发展的一个热点（2021年诺贝尔化学奖授予方向）。本课题组的一个主要研究方向就是利用手性Brønsted酸类催化剂，利用其作为质子酸催化剂、手性阴离子等多种参与不对称反应的方式，发展（动态）动力学拆分、动态动力学不对称转化、对映选择性去对称化等策略，实现具有四取代手性中心、轴手性、平面手性、螺旋手性和固有手性分子的精准不对称构建。

2）糖化学中选择性控制（Selectivity Control in Carbohydrate Chemistry）

糖作为组成生命体的一类重要大分子相比于蛋白质、DNA等具有更加复杂的化学特性，包括其连接的区域选择性、糖苷化反应的立体选择性等。本课题组的一个研究兴趣就是利用催化剂实现糖类分子的高效区域选择性以及立体选择性合成。

课题组主页：https://www.x-mol.com/groups/Yang_Xiaoyu

欢迎有志于以上研究领域的博士后、研究生以及本科生加入本课题组！

发表论文 (Publishcations)

After joining ShanghaiTech:

49. Zidan Ye, Wansen Xie, Wei Liu, Changyu Zhou, Xiaoyu Yang*, Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization, Adv. Sci. 2024, 2403125.

48. Shaoze Yu, Mengyao Yuan, Wansen Xie, Zidan Ye, Tianren Qin, Na Yu, Xiaoyu Yang*, Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations, Angew. Chem. Int. Ed. 2024, 63, e202410628.

47. Wansen Xie, Jinmiao Zhou, Wei Liu, Tianren Qin, Xiaoyu Yang*, Divergent asymmetric synthesis of heterohelicenes via sequential organocatalyzed Povarov reaction and aromatization, Cell Rep. Phy. Sci. 2024, 5, 101993.

46. Jinmiao Zhou, Mengyao Tang, Xiaoyu Yang*, Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1,5]diazocines, Chin. J. Chem. 2024, 42, 1953-1959. (Invited as Emerging Investigators in 2024, selected as Breaking Report)

45. Zidan Ye, Wansen Xie, Donglei Wang, Hua Liu, and Xiaoyu Yang*, Atroposelective Synthesis of Diarylamines via Organocatalyzed Electrophilic Amination, ACS Catal. 2024, 14, 4958-4967.

44. Mengyao Tang, Mengyao Yuan, Shibin Hong, Qianwen Jiang, Huanchao Gu, and Xiaoyu Yang*, Kinetic Resolution of Sulfoximines via Asymmetric Organocatalyzed Formation of Benzothiadiazine-1-oxides, Org. Lett. 2024, 26, 1914–1919.

43. Dekun Zhang#, Jinmiao Zhou#, Tianren Qin, Xiaoyu Yang*, Asymmetric synthesis of saddle-shaped eight-membered azaheterocycles via (dynamic) kinetic resolution, Chem. Catal. 2024, 4, 100827.

42. Qianwen Jiang, Dekun Zhang, Mengyao Tang, Hua Liu, Xiaoyu Yang*, (Parallel) kinetic resolution of 3,3-disubstituted indolines via organocatalyzed reactions with azodicarboxylates, Sci. China Chem. 2024, 67, 973-980.

41. Mengyao Tang, Xiaoyu Yang,* One-step synthesis of indole atropisomers with vicinal diaxes via Co-catalyzed C–H activation, Chem. Catal. 2023, 3, 100754. (Invited preview)

40. Guosong Shen , Faqian He, Wansen Xie, Huanchao Gu, and Xiaoyu Yang*, Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis, ACS Catal. 2023, 13, 12472–12480.

39. Mengyao Tang and Xiaoyu Yang*, Catalytic Enantioselective Synthesis of Inherently ChiralMolecules: Recent Advances, Eur. J. Org. Chem. 2023, e202300738. (invited review)

38. Shaoze Yu, Hanyang Bao, Dekun Zhang and Xiaoyu Yang*, Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination, Nat. Commun. 2023, 14, 5239.

37. Zidan Ye, Wei Liu, Huanchao Gu, and Xiaoyu Yang*, Enantioselective Dearomatization of Substituted Phenols via Organocatalyzed Electrophilic Amination, Org. Lett. 2023, 25, 5838–5843.

36. Wei Liu,# Tianren Qin,# Wansen Xie, Jinmiao Zhou, Zidan Ye and Xiaoyu Yang*, Enantioselective Synthesis of Azahelicenes through Organocatalyzed Multicomponent Reactions, Angew. Chem. Int. Ed. 2023, 62, e202303430.

35. Qianwen Jiang, Wansen Xie and Xiaoyu Yang*, Asymmetric Synthesis of Highly Sterically Congested α-Tertiary Amines via Organocatalyzed Kinetic Resolution, Chem. Commun., 2023, 59, 4762-4765.

Graphical abstract:Asymmetric synthesis of highly sterically congested α-tertiary amines via organocatalyzed kinetic resolution

34. Hanyang Bao, Yunrong Chen, Xiaoyu Yang*, Catalytic Asymmetric Synthesis of Axially Chiral Diaryl Ethers through Enantioselective Desymmetrization, Angew. Chem. Int. Ed. 2023, 62, e202300481.

33. Dekun Zhang , Ying-Bo Shao, Wansen Xie, Yunrong Chen, Wei Liu, Hanyang Bao, Faqian He, Xiao-Song Xue*, and Xiaoyu Yang* Remote Enantioselective Desymmetrization of 9,9-Disubstituted 9,10-Dihydroacridines through Asymmetric Aromatic Aminations, ACS Catal. 2022, 12, 14609–14618.

32. Wei Liu, Tianren Qin, Wansen Xie, Xiaoyu Yang* Catalytic Enantioselective Synthesis of Helicenes, Chem. Eur. J. 2022, e202202369 (Invited Review)

31. Shaoze Yu, Guosong Shen, Faqian He and Xiaoyu Yang* Asymmetric Synthesis of Planar-chiral Macrocycles via Organocatalyzed Enantioselective Macrocyclization, Chem. Commun. 2022, DOI: 10.1039/D2CC01690G.

30. Jinglei Xie#, Zheng Guo#, Wei Liu, Dekun Zhang, Yu-Peng He*, Xiaoyu Yang* Kinetic Resolution of 1,2-Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines, Chin. J. Chem. 2022, 40, 1674-1680.

29. Yunrong Chen, Wei Liu, Xiaoyu Yang*, Recent Advances in Kinetic Resolution of Tertiary Alcohols, Chin. J. Org. Chem., 2022, 42, 679-697. (Invited Review, Cover Paper)

28. Donglei Wang, Ying-Bo Shao, Yunrong Chen, Xiao-Song Xue*, Xiaoyu Yang*, Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination. Angew. Chem. Int. Ed. 2022, 61, e2022010.

27. Wei Liu , Donglei Wang , Dekun Zhang , Xiaoyu Yang* Catalytic Kinetic Resolution and Desymmetrization of Amines, Synlett 2022, DOI: 10.1055/a-1790-3230 (Invited account)

26. Qianwen Jiang, Tianren Qin and Xiaoyu Yang*, Asymmetric Synthesis of Hydroquinazolines Bearing C4-Tetrasubstituted Stereocenters via Kinetic Resolution of α-Tertiary Amines, Org. Lett. 2022, 24, 625–630.

25. Faqian He, Guosong Shen and Xiaoyu Yang*, Asymmetric Aminations and Kinetic Resolution of Acyclic α-Branched Ynones, Chin. J. Chem. 2022, 40, 15.

24. Jiawen Wang, Faqian He and Xiaoyu Yang*, Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides, Nat. Commun. 2021, 12, 6700.

23. Yunrong Chen*, Xueqian Ye, Faqian He and Xiaoyu Yang*, Asymmetric synthesis of oxazolines bearing α-stereocenters through radical addition–enantioselective protonation enabled by cooperative catalysis, Org. Chem. Front. 2021, DOI: 10.1039/D1QO00970B

22. Zheng Guo, Jinglei Xie, Tao Hu, Yunrong Chen,* Houchao Tao* and Xiaoyu Yang*, Kinetic resolution of N-aryl β-amino alcohols via asymmetric aminations of anilines, Chem. Commun. 2021, 57, 9394-9397.

21. Faqian He, Jiawen Wang, Fang Zhou, Houchao Tao* and Xiaoyu Yang*, Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters, Org. Chem. Front. 2021, 8, 5377-5382.

20. Mengyao Tang, Huanchao Gu, Shunlong He, Subramani Rajkumar, Xiaoyu Yang* Asymmetric Enamide-Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols, Angew. Chem. Int. Ed. 2021, 60, 21334 – 21339. (Hot Paper)

19. Yongkai Pan, Donglei Wang, Yunrong Chen, DeKun Zhang, Wei Liu, and Xiaoyu Yang*, Kinetic Resolution of α-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines, ACS Catal. 2021, 11, 8843-8848.

18. Chaofan Zhu , Wei Liu, Fei Zhao, Yunrong Chen*, Houchao Tao*, Yu-Peng He*, Xiaoyu Yang* Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations Org. Lett. 2021, 23, 4104–4108.

17. Dekun Zhang, Yunrong Chen, Yongning Lai, Xiaoyu Yang* Enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-propanediamines via asymmetric para-aminations of anilines, Cell Rep. Phy. Sci.2021, 2, 100413.

16. Wei Liu, Xiaoyu Yang*, Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids, Asian J. Org. Chem. 2021, 10, 692-710. (invited review, VIP paper)

15. Yunrong Chen, Chaofan Zhu, Zheng Guo, Wei Liu, Xiaoyu Yang* Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution via Organocatalyzed Kinetic Resolution, Angew. Chem. Int. Ed., 2021, 60, 5268 –5272.

14. Jiawen Wang#, Sujuan Zheng#, Subramani Rajkumar, Jinglei Xie, Na Yu, Qian Peng* and Xiaoyu Yang* Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies, Nat. Commun.2020, 11, 5527.

13. Yongkai Pan, Qianwen Jiang, Subramani Rajkumar, Chaofan Zhu, Jinglei Xie, Shaoze Yu, Yunrong Chen, Yu-Peng He* and Xiaoyu Yang* Kinetic Resolution of 2-N-Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines, Adv. Syn. Catal. 2021, 363, 200-207 (VIP paper)

12. Wei Liu, Qianwen Jiang, Xiaoyu Yang*, Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation, Angew. Chem. Int. Ed., 2020, 59, 23598 – 23602

11. Xueqian Ye Yongkai Pan Yunrong Chen Xiaoyu Yang*, Enantioselective Construction of Sulfur‐Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α‐Sulfanyl Cyclic Ketones, Adv. Syn. Catal. 2020, 362, 3374-3379.

10. Shunlong He, Huanchao Gu, Yu-Peng He*, and Xiaoyu Yang*，Asymmetric Aza-Diels–Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N–H Ketimines Catalyzed by Chiral Phosphoric Acids，Org. Lett., 2020, 22, 5633–5639.

9. Donglei Wang, Qianwen Jiang and Xiaoyu Yang*，Atroposelective synthesis of configurationally stable nonbiaryl N-C atropisomers through direct asymmetric aminations of 1,3-benzenediamines, Chem Commun, 2020, 56, 6201-6204. (Selected as “Chem Commun HOT Articles' by editors)

8. Subramani Rajkumar#, Mengyao Tang# and Xiaoyu Yang*, Chiral Phosphoric Acid-Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines, Angew. Chem. Int. Ed. 2020, 59, 2333-2337.

7. Xueqian Ye, Yongkai Pan and Xiaoyu Yang*, Direct enantioselective Mannich reactions of α-azido cyclic ketones: asymmetric construction of chiral azides possessing an α-quaternary stereocenter, Chem. Commun. 2020, 56, 98-101.

6. Donglei Wang#, WeiLiu#, MengyaoTang, NaYu, XiaoyuYang*, Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalysed para-Aminations of Anilines and Phenols, iScience, 2019, 22, 195-205.

5. Subramani Rajkumar#, Shunlong He# and Xiaoyu Yang* Kinetic Resolution of Tertiary 2-Alkoxycarboxamido-allylic Alcohols by Chiral Phosphoric Acid Catalyzed Intramolecular Transesterification. Angew. Chem. Int. Ed. 2019, 58, 10315 –10319.

4. Wei Liu, Subramani Rajkumar, Weihu Wu, Ziyu Huang, and Xiaoyu Yang*, Asymmetric Synthesis of β-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel–Crafts Alkylation Reactions, Org. Lett. 2019, 21, 10, 3563-3567.

3. Subramani Rajkumar#, Jiawen Wang#, Xiaoyu Yang*, Asymmetric Transformations of α-Hydroxy Enamides Catalyzed by Chiral Brønsted Acids, Synlett 2019, 30(08): 869-874 (invited synpact paper)

2. Subramani Rajkumar#, Jiawen Wang#, Sujuan Zheng, Donglei Wang, Xueqian Ye, Xuejiao Li, Qian Peng,* and Xiaoyu Yang*, Regioselective and Enantioselective Synthesis of β-Indolyl Cyclopentenamides by Chiral Anion Catalysis. Angew. Chem. Int. Ed. 2018, 57, 13489 –13494

1. Shixian Lin#; Xiaoyu Yang#, S. Jia, A.M. Weeks, M. Hornsby, P.S. Lee, R.V. Nichiporuk, A.T. Iavarone, J.A. Wells, F.D. Toste, C.J. Chang, Redox-based reagents for chemoselective methionine bioconjugation. Science 2017, 355, 597-602 (# contribute equally)

Selected works before joining ShanghaiTech:

Xiaoyu Yang and F. Dean Toste*. Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid. Chem. Sci. 2016, 7, 2653-2656.
Xiaoyu Yang, F. Dean Toste*. Direct Asymmetric Amination of α-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid. J. Am. Chem. Soc. 2015, 137, 3205-3208.
Xiaoyu Yang#, Tao Wu#, Robert J. Phipps, F. Dean Toste*.Advances in Catalytic Enantioselective Fluorination, Mono, Di, and Trifluoromethylation, and Trifluoromethylthiolation Reactions. Chem. Rev. 2015, 115, 826-870.
Xiaoyu Yang#, Robert J. Phipps#, F. Dean Toste*. Asymmetric Fluorination of α-Branched Ketones Enabled by a Synergistic Combination of Chiral Anion Phase-Transfer Catalysis and Enamine Catalysis using Protected Amino Acids. J. Am. Chem. Soc. 2014, 136, 5225-5228.
Xiaoyu Yang, Boqiao Fu, and Biao Yu*.Total Synthesis of Landomycin A, a Potent Antitumor Angucycline Antibiotic. J. Am. Chem. Soc. 2011, 133, 12433-12435.