Yan Qiaozhi, Shen Xin, Zi Guofu, Hou Guohua
Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
School of Water Resources and Environment, Hebei GEO University, Shijiazhuang, 050031, P. R. China.
Chemistry. 2020 May 12;26(27):5961-5964. doi: 10.1002/chem.202000703. Epub 2020 Apr 28.
A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.
已开发出一种由铑-(S)-DTBM-联二萘酚膦配合物催化的α,β-不饱和硼酸酯的高度对映选择性氢化反应。(Z)-α,β-和β,β-二取代的底物均可成功氢化，以优异的对映选择性得到手性硼酸酯，对映体过量值高达98%。此外，所得到的手性硼酸酯作为重要的通用合成中间体，可成功转化为相应的手性醇、胺及其他重要衍生物，且对映选择性得以保持。
