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

Org Lett

Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Published: March 2025

The asymmetric hydrogenation (AH) of cyclic -alkyl imines offers an elegant and efficient method to afford chiral amines, especially for -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 -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.

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http://dx.doi.org/10.1021/acs.orglett.5c00044DOI Listing

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

Org Lett

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