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

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

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Although it offers a direct route to access synthetically valuable a-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.

Asymmetric transfer hydrogenationAsymmetric hydrogenationα-Chiral primary amineNH imines2-(1-Aminoalkyl)anilines

Mangang Zhang、Hui Li、Keqin Wu、Nianxin Rong、Shaoquan Lin、Hua Yang、Qin Yin

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College of Chemistry and Chemical Engineering,Central South University,Changsha,Hunan 410083,China

Faculty of Pharmaceutical Sciences,Shenzhen University of Advanced Technology,Shenzhen,Guangdong 518055,China

Shenzhen Institute of Advanced Technology,Chinese Academy of Sciences,Shenzhen,Guangdong 518055,China

2024

10.1002/cjoc.202400338

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(18)