通过镍催化的不对称氢化合成手性β-硼化羧酸酯
Synthesis of Chiral β-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation.
作者信息
Han Zhengyu, Liu Gang, Zhang Xianghe, Li Anqi, Dong Xiu-Qin, Zhang Xumu
机构信息
Key Laboratory of Biomedical Polymers, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences , Wuhan University , Wuhan , Hubei 430072 , P. R. China.
Department of Chemistry, Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , Guangdong 518055 , P. R. China.
出版信息
Org Lett. 2019 Jun 7;21(11):3923-3926. doi: 10.1021/acs.orglett.9b00994. Epub 2019 May 22.
The highly efficient Ni-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters was successfully developed using ( S, S)-Ph-BPE as the ligand. A series of chiral β-borylated carboxylic esters were obtained with high yields (94%-99% yields) and excellent enantioselectivities (89%-99% ee). The gram-scale asymmetric hydrogenation with a low catalyst loading (0.25 mol %) and synthetic transformation of hydrogenation product demonstrated the great synthetic utility of this methodology.
使用（S，S）-Ph-BPE作为配体，成功开发了β-硼酸酯取代的α，β-不饱和羧酸酯的高效镍催化不对称氢化反应。获得了一系列手性β-硼化羧酸酯，产率高（94%-99%），对映选择性优异（89%-99% ee）。低催化剂负载量（0.25 mol%）的克级不对称氢化反应以及氢化产物的合成转化证明了该方法具有巨大的合成实用性。
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