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Alternative TitleDevelopment of Efficient Asymmetric Suzuki-Miyaura Cross-Coupling and Applications in Synthesis
Source Publication有机化学
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
Indexed BySCI
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Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
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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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