手性四磷酸二铑催化α-芳基重氮乙酸酯的对映选择性硅氢键插入反应
Chiral Dirhodium Tetraphosphate-Catalyzed Enantioselective Si-H Bond Insertion of α-Aryldiazoacetates.
作者信息
Yang Liang-Liang, Cao Jin, Zhao Tian-Yuan, Zhu Shou-Fei, Zhou Qi-Lin
机构信息
Frontiers Science Center for New Organic Matter, State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
出版信息
J Org Chem. 2021 Jul 16;86(14):9692-9698. doi: 10.1021/acs.joc.1c00967. Epub 2021 Jun 29.
A highly enantioselective Si-H bond insertion reaction of α-aryldiazoacetates catalyzed by chiral spiro dirhodium tetraphosphate was developed. Various chiral α-silyl esters were prepared with high yield (up to 92%) and excellent enantioselectivity (up to >99% ee) through this protocol. It is noteworthy that the 2-substituted aryl diazoacetates, which are challenging substrates for other chiral dirhodium catalysts, also exhibited good results in this reaction. This work represents one of the few successful applications of chiral dirhodium phosphates in asymmetric catalysis.
开发了一种由手性螺环四磷酸二铑催化的α-芳基重氮乙酸酯的高对映选择性硅氢键插入反应。通过该方法制备了各种手性α-硅基酯，产率高（高达92%），对映选择性优异（高达>99% ee）。值得注意的是，2-取代芳基重氮乙酸酯是其他手性二铑催化剂难以处理的底物，在该反应中也表现出良好的结果。这项工作是手性磷酸二铑在不对称催化中少数成功的应用之一。
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