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学科主题: 金属有机化学
题名: 发展高效的不对称Suzuki-Miyaura偶联反应及其合成应用
其他题名: Development of Efficient Asymmetric Suzuki-Miyaura Cross-Coupling and Applications in Synthesis
作者: XU GUANGQING; ZHAO QING; 汤文军
刊名: 有机化学
发表日期: 2014
DOI: 10.6023/cjoc201406030
卷: 34, 期:10, 页:1919-1940
收录类别: SCI
英文摘要: A 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.
语种: 中文
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39134
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所

Recommended Citation:
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.
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