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Taming Chiral Quaternary Stereocenters via Remote H-Bonding Stereoinduction in Palladium-Catalyzed (3+2) Cycloadditions

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成果类型:
期刊论文
作者:
Xiao, Yu-Qing;Li, Miao-Miao;Zhou, Zheng-Xin;Li, Yu-Jie;Cao, Meng-Yue;...
通讯作者:
Rao, Li(raoli@mail.ccnu.edu.cn);Lu, Liang-Qiu(luliangqiu@mail.ccnu.edu.cn)
作者机构:
[Lu, Liang-Qiu; Rao, Li; Zhou, Zheng-Xin; Xiao, Wen-Jing; Li, Yu-Jie; Liu, Xiao-Peng; Xiao, Yu-Qing] Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
[Li, Miao-Miao] Zhengzhou Univ, Henan Inst Adv Technol, Div Mol Catalysis & Synth, Zhengzhou 45000, Peoples R China.
[Cao, Meng-Yue; Liu, Xiao-Peng] Westlake Univ, Sch Sci, Hangzhou 310024, Peoples R China.
[Lu, Liang-Qiu] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China.
[Lu, Liang-Qiu] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China.
通讯机构:
[Dr. Li Rao; Prof. Liang-Qiu Lu] C
CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079 China<&wdkj&>State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China<&wdkj&>School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China<&wdkj&>CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079 China
语种:
英文
关键词:
Asymmetric Cycloaddition;D-A Cyclopropane;H-Bonding;Palladium Catalysis;Quaternary Stereocenters
期刊:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN:
1433-7851
年:
2023
卷:
62
期:
3
页码:
e202212444-
基金类别:
National Natural Science Foundation of China [21822103, 21820102003, 91956201, 22271113]; Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019]; Natural Science Foundation of Hubei Province [2017AHB047]; Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis
机构署名:
本校为第一机构
院系归属:
化学学院
摘要:
Ring-opening transformations of donor-acceptor (D-A) cyclopropanes enable the rapid assembly of complex molecules. However, the enantioselective formation of chiral quaternary stereocenters using substrates bearing two different acceptors remains a challenge. Herein, we describe the first palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition of vinyl cyclopropanes bearing two different electron-withdrawing groups, a subset of D-A cyclopropanes. The key to the success of this reaction is the remote stereoinduction throug...

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