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

journal contribution
posted on 2025-04-02, 08:37 authored by Jitao Yang, Yanan Guo, Zheng Wang, Yizhou Wang, Dexin Fu, Qingbin Liu, Gregory SolanGregory Solan, Yanping Ma, Wen-Hua Sun
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.

History

Author affiliation

College of Science & Engineering Chemistry

Version

  • AM (Accepted Manuscript)

Published in

Organic Letters

Volume

27

Issue

11

Pagination

2564–2568

Publisher

American Chemical Society (ACS)

issn

1523-7060

eissn

1523-7052

Copyright date

2025

Available date

2026-03-12

Spatial coverage

United States

Language

en

Deposited by

Dr Gregory Solan

Deposit date

2025-03-28

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