Manganese-Catalyzed Asymmetric Hydrogenation of Pyridyl Cyclic N -Alkyl Imines: A Direct Route to S -Nicotine and Derivatives

作者：Jitao Yang, Yanan Guo, Zheng Wang, Yizhou Wang, Dexin Fu, Qingbin Liu, Gregory A. Solan, Yanping Ma, Wen‐Hua Sun · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c00044 · 被引用次数：11 · 研究领域：Asymmetric Hydrogenation and Catalysis、Asymmetric Synthesis and Catalysis、Catalytic C–H Functionalization Methods

The asymmetric hydrogenation (AH) of cyclic N -alkyl imines offers an elegant and efficient method to afford chiral amines, especially for S -nicotine and its derivatives. However, this approach remains an ongoing challenge due to undesirable coordination of pyridyl-containing substrates to the active metal catalyst. Herein, we disclose a manganese-catalyzed AH that allows access to S -nicotine and other chiral α-(hetero)aryl pyrrolidines and provides an example of a base–metal catalyst that displays superior performance to its noble metal counterparts.