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发展高效的不对称Suzuki-Miyaura偶联反应及其合成应用
Alternative TitleDevelopment of Efficient Asymmetric Suzuki-Miyaura Cross-Coupling and Applications in Synthesis
XU GUANGQING; ZHAO QING; 汤文军
2014
Source Publication有机化学
Volume34Issue:10Pages:1919-1940
Other AbstractA series of structurally rigid, sterically bulky biaryl monophosphorus ligands were designed and synthesized to investigate the reactivity and stereoselectivity of asymmetric Suzuki-Miyaura cross-coupling reaction. High efficiencies were achieved in sterically demanding cross-couplings for the synthesis of tetra-ortho-substituted biaryls with various functionalities. Sterically demanding aryl-alkyl Suzuki-Miyaura couplings between di-ortho-substituted aryl halides and secondary alkylboronic acids were also successful. In achieving efficient asymmetric Suzuki-Miyaura coupling, we implemented a new concept by employment of a chiral biaryl monophosphorus ligand developed in the group as well as utilization of a secondary interaction between two coupling partner. Using a pi-pi interaction of a benzooxazolidinone substituent with one aryl partner, we developed enantioselective biaryl couplings containing ortho-carbonyl substituents. High enantioselectivities were also achieved in biaryl coupling containing ortho-oxy substituents by utilizing a polar-it interaction between a polar bis(2-oxo-3-oxazolidinyl)phosphonic (BOP) substituent and one aryl partner. The methodology enabled us for the first time to implement efficient asymmetric Suzuki-Miyaura coupling in total synthesis and accomplish the syntheses of chiral biaryl natural products korupensamines A and B, ultimately a concise and stereoselective synthesis of michellamine B.
Subject Area金属有机化学
DOI10.6023/cjoc201406030
URL查看原文
Indexed BySCI
Language中文
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Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39134
Collection金属有机化学国家重点实验室
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
XU GUANGQING,ZHAO QING,汤文军. 发展高效的不对称Suzuki-Miyaura偶联反应及其合成应用[J]. 有机化学,2014,34(10):1919-1940.
APA XU GUANGQING,ZHAO QING,&汤文军.(2014).发展高效的不对称Suzuki-Miyaura偶联反应及其合成应用.有机化学,34(10),1919-1940.
MLA XU GUANGQING,et al."发展高效的不对称Suzuki-Miyaura偶联反应及其合成应用".有机化学 34.10(2014):1919-1940.
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