镍催化的不对称转移氢化和 - 亚磺酰亚胺与醇的 α-选择性氘代：获得 α-氘代手性胺。
Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration of -Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines.
机构信息
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, P. R. China.
出版信息
Org Lett. 2020 Nov 6;22(21):8278-8284. doi: 10.1021/acs.orglett.0c02921. Epub 2020 Oct 12.
A nickel-catalyzed enantioselective transfer hydrogenation and deuteration of -sulfonyl imines was developed. Excellent α-selectivity and high deuterium content were achieved by using inexpensive 2-propanol- as a deuterium source. As a highlight, no deuteration of β-C-H and the remote C-H of -sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with DO. Mechanism studies indicated a stepwise pathway through the [Ni-D] intermediate.
发展了镍催化的 -亚磺酰亚胺的对映选择性转移氢化和氘代反应。通过使用廉价的 2-丙醇作为氘源，实现了优异的 α-选择性和高氘含量。值得一提的是，-亚磺酰胺的 β-C-H 和远程 C-H 没有发生氘代反应，这是使用其他亚胺或通过与 DO 的氢同位素交换难以实现的。机理研究表明，该反应是通过 [Ni-D] 中间体的分步途径进行的。
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