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理学院专题学术讲座 | 游书力:催化不对称去芳构化反应

时间

2021年6月17日(周四)
下午16:00-17:30

地点

西湖大学云栖校区5号楼一楼学术报告厅

主持

西湖大学理学院PI 陆海华 博士

受众

全体师生

分类

学术与研究

理学院专题学术讲座 | 游书力:催化不对称去芳构化反应

时间2021年6月17日(周四)下午16:00-17:30

Time16:00-17:30, Thursday, June 17th, 2021

主持人: 西湖大学理学院PI 陆海华 博士

Host: Dr. Haihua Lu, PI of School of Science, Westlake University

地址:西湖大学云栖校区5号楼一楼学术报告厅

Venue: Lecture Hall, 1F, Building 5, Yunqi Campus, Westlake University


游书力 研究员

中科院上海有机所金属有机国家重点实验室,上海市零陵路345号

Prof. Shu-Li You,

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Lu, Shanghai, China

E-mail: slyou@mail.sioc.ac.cn


主讲人/Speaker

游书力研究员,1996年本科毕业于南开大学化学系;2001年自中科院上海有机所获得博士学位(导师:戴立信院士)后,在美国Scripps Research Institute 从事博士后研究(导师: Professor Jeffery W. Kelly);2004年2月被聘任为 Genomics Institute of the Novartis Research Foundation (GNF) 独立课题组负责人;2006年4月起聘为中科院上海有机所研究员,并于2017年起任金属有机国家重点实验室主任。游书力研究员长期从事手性催化研究,提出“催化不对称去芳构化”新概念,开发多个原创手性配体,十余个已实现商品化,发展系列手性催化新反应,可便捷高效地合成多种天然产物及药物分子,其成果被多部教材和专著收录并被国际同行广泛应用。发表论文300余篇,被他引17000余次,H-index为82(统计截止于2021年5月),主编英文专著两部,获授权中国发明专利三十余项,受邀做大会及邀请报告一百余次。获2015年英国皇家化学会默克奖、第十四届中国青年科技奖、2016年何梁何利基金青年创新奖、2017年国家自然科学二等奖(第一完成人)、2017/2018 Novartis Chemistry Lectureship、第十六届上海市科技精英及首届科学探索奖。


Prof. Shu-Li You received his BSc in chemistry from Nankai University in 1996. He obtained his PhD from the Shanghai Institute of Organic Chemistry (SIOC) in 2001 under the supervision of Prof. Li-Xin Dai before doing postdoctoral studies with Prof. Jeffery W. Kelly at The Scripps Research Institute. From 2004, he worked at the Genomics Institute of the Novartis Research Foundation as a Principal Investigator before returning to SIOC in 2006. Since January 2017, He has been appointed as the Director of the State Key Laboratory of Organometallic Chemistry. His current research interests include asymmetric catalysis, synthetic methodology, natural product synthesis, as well as medicinal chemistry. Prof. Shu-Li You has published over 300 peer-reviewed papers and edited two books, and applied over 30 Chinese patents as a co-inventor. Dr. You’s papers have received total citations by others over 17000 and his h-index is 82 (until May 2021). He is the recipient of AstraZeneca Excellence in Chemistry Award (2011), RSC Merck Award (2015), Ho Leung Ho Lee Foundation Prize for Scientific and Technological Innovation (2016) and Novartis Chemistry Lectureship (2017/2018).

讲座摘要/Abstract:

芳香化合物是来源于化石资源的基础化学原料,结构丰富、种类多样。基于芳香化合物的化学转化一直是有机化学核心研究内容,其中亲电芳香取代反应是最常见的转化方法,可以在芳环上引入不同的官能团,产物保留芳香性。含有季碳中心的螺环和多环骨架在天然产物、药物等功能分子中广泛存在,但从芳香化合物出发直接合成这类螺环和多环骨架分子的方法极其有限,发展全新的芳香化合物转化新概念、新方法具有重要意义。去芳构化反应可以从二维平面分子出发合成三维立体且高度官能团化产物,构筑全新的分子骨架,极大拓宽了产物化学空间。这一过程需要破坏芳香性,因而极其挑战。克服去芳构化过程中的高能垒,避免去芳构化产物再芳构化,实现化学、区域和立体选择性控制是去芳构化反应的关键科学问题。本课题组首次提出了“催化不对称去芳构化(CADA)”概念,发展了系列不对称去芳构化新反应,为药物研发提供新颖分子骨架的化合物库。CADA概念被国内外多个课题组应用于发展新型不对称催化反应、催化体系及全合成研究。


Dearomatization reactions are widely recognized as powerful methods for the synthesis of highly functionalized three-dimensional structures from simple planar aromatic compounds. Among those, catalytic asymmetric dearomatization (CADA) reactions are very attractive due to the abundance and ready availability of aromatic compounds and the direct access to enantiopure polycycles and spirocycles offered by them. That latter are frequently the key motifs in biologically active natural products and pharmaceuticals. However, due to the extra stability of “aromaticity” of the arenes, their dearomatization reactions with good enantioselective control has been a great challenge. In this talk, the application of TM-catalyzed allylic substitution reactions in dearomatization process will be reported. The dearomatization reactions of indoles, pyrroles, phenols, naphthols, and pyridines have been achieved, affording various highly functionalized heterocycles bearing all-carbon quaternary chiral centers in most of the cases. These results provide not only the efficient synthesis of highly enantioenriched spiro- or polycycles, but also a novel concept in asymmetric catalysis.

References:

[1] You, S.-L. (2016) Asymmetric Dearomatization Reactions, Wiley-VCH.

[2] Tu, H.-F.; Zhang, X.; Zheng, C.; Zhu, M.; You, S.-L. Nature Catal. 2018, 1, 601.

[3] Tu, H.-F.; Yang, P.; Lin, Z.-H.; Zheng, C.; You, S.-L. Nature Chem. 2020, 12, 838.

[4] Jiang, R.; Ding, L.; Zheng, C.; You, S.-L. Science 2021, 371, 380-386..

讲座联系人/Contact:

理学院,彭卓,邮箱:pengzhuo@westlake.edu.cn

School of Science, Zhuo Peng, Email: pengzhuo@westlake.edu.cn