Manganese-Catalyzed Asymmetric Hydrogenation of Pyridyl Cyclic <i>N</i>-Alkyl Imines: A Direct Route to <i>S</i>-Nicotine and Derivatives
Jitao Yang, Yanan Guo, Zheng Wang, Yizhou Wang, Dexin Fu, Qingbin Liu, Gregory A. Solan, Yanping Ma, Wen‐Hua Sun
Abstract
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.
Topics & Concepts
ChemistryCatalysisAlkylManganeseNicotineAsymmetric hydrogenationOrganic chemistryMedicinal chemistryCombinatorial chemistryEnantioselective synthesisBiologyNeuroscienceAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods