Asymmetric Transfer Hydrogenation of Stable NH Imines for the Synthesis of Enantiopure α-Chiral Primary Amines  

作　　者：Mangang Zhang Hui Li Keqin Wu Nianxin Rong Shaoquan Lin Hua Yang Qin Yin 

机构地区：[1]College of Chemistry and Chemical Engineering,Central South University,Changsha,Hunan 410083,China [2]Faculty of Pharmaceutical Sciences,Shenzhen University of Advanced Technology,Shenzhen,Guangdong 518055,China [3]Shenzhen Institute of Advanced Technology,Chinese Academy of Sciences,Shenzhen,Guangdong 518055,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2211-2216,共6页中国化学（英文版）

基　　金：the National Natural Science Foundation of China(22071097,22271307,22378432);the Guangdong Basic and Applied Basic Research Foundation(2021B1515020062);the Shenzhen Science and Technologyy Program(JCYJ20220818100804010).

摘　　要：Although it offers a direct route to access synthetically valuableα-chiral primary amines,asymmetric transfer hydrogenation of NH imines has been rarely studied,due in large part to the inaccessibility and instability of NH imines.Herein,we report a Rh-catalyzed asymmetric transfer hydrogenation of a kind of novel and stable NH imines which are prepared via condensation of easily available sulfonylated 2'-aminoacetophenones with NH3 in methanol.With this method,enantioenriched chiral 2-(1-aminoalkyl)anilines,which are privileged pharmacore groups,have been synthesized with good functional group compatibility,and with up to 99%ee.A gram-scale reaction using 0.2 mol%of catalyst has been successfully performed to highlight the practicality.Furthermore,the products can be derivatized into enantiopure bioactive molecules as well as chiral tridentate ligands for metal catalysis.

关 键 词：Asymmetric transfer hydrogenation Asymmetric hydrogenation α-Chiral primary amine NH imines 2-(1-Aminoalkyl)anilines 

分 类 号：O62[理学—有机化学]