Huang Yinhua, Wang Lijun, Li Junbao, Qiu Huayu, Leung Pak-Hing
College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
ACS Omega. 2020 Jun 23;5(26):15936-15941. doi: 10.1021/acsomega.0c01124. eCollection 2020 Jul 7.
Chiral diarylmethylamines are of great interest because of their prevalence in biological and pharmaceutical sciences. Herein, we report a -palladacycle-catalyzed enantioselective synthesis of chiral diarylmethylamines via asymmetric arylation of -protected imines with arylboronic acids. The -palladacycle showed high reactivity (up to 99% yield) and enantioselectivity (up to 99% ) toward this arylation, enabling the tolerance of a wide range of functionalities, providing a convenient and efficient access to enantiomerically enriched diarylmethylamines. The absolute configuration of the product was well rationalized by the proposed stereochemical pathway and the catalytical cycle.
手性二芳基甲胺因其在生物和制药科学中的广泛存在而备受关注。在此,我们报道了一种通过钯环催化的、由芳基硼酸对保护的亚胺进行不对称芳基化反应来对映选择性合成手性二芳基甲胺的方法。该钯环对此芳基化反应表现出高反应活性(产率高达99%)和对映选择性(高达99%),能够耐受多种官能团,为对映体富集的二芳基甲胺提供了一种方便且高效的合成途径。产物的绝对构型通过所提出的立体化学途径和催化循环得到了很好的解释。