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钯催化的通过炔丙基苯甲酸酯与硼酸酯的偶联反应构建三取代烯丙基化合物的对映选择性合成。

Pd-Catalyzed Enantioselective Syntheses of Trisubstituted Allenes via Coupling of Propargylic Benzoates with Organoboronic Acids.

机构信息

Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, PR China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.

出版信息

J Am Chem Soc. 2020 May 27;142(21):9763-9771. doi: 10.1021/jacs.0c02876. Epub 2020 May 14.

Abstract

Enabled by the newly developed ligand, Ming-Phos, the first example of palladium-catalyzed highly enantioselective coupling of racemic propargylic benzoates with organoboronic acids for chiral allenes synthesis has been developed. Excellent asymmetric induction has been achieved with a decent substrate scope. Synthetic potentials for the construction of polycyclic compounds with multiple chiral centers have been demonstrated.

摘要

受新开发的配体 Ming-Phos 的推动,首例钯催化的外消旋丙炔基苯甲酸酯与硼酸酯的高对映选择性偶联反应,用于手性丙二烯的合成已经被开发出来。该反应具有良好的底物范围,实现了优异的不对称诱导。该方法为构建具有多个手性中心的多环化合物提供了合成潜力。

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