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

The asymmetric hydrogenation (AH) of cyclic <i>N</i>-alkyl imines offers an elegant and efficient method to afford chiral amines, especially for <i>S</i>-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 <i>S</i>-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.<p></p>