手性双齿硼基配体促进的铱催化环丙烷 C(sp3)-H 硼化反应的对映选择性。
Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp)-H Borylation of Cyclopropanes.
机构信息
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute , Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
出版信息
J Am Chem Soc. 2019 Jul 10;141(27):10599-10604. doi: 10.1021/jacs.9b04549. Epub 2019 Jul 1.
We herein report an Ir-catalyzed enantioselective C(sp)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.
我们在此首次报道了使用手性双齿硼配体的 Ir 催化的环丙甲酰胺的 C(sp^2)-H 硼化反应的对映选择性。该反应可以兼容具有α-季碳中心的各种底物，从而以良好到优异的对映选择性提供β-硼化产物。我们还证明，硼化产物可用作参与 C-B 键的立体特异性转化的多功能前体，包括生物活性化合物 Levomilnacipran 的合成。
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