Nickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines

Bowen Li, Jianzhong Chen, Zhenfeng Zhang, Ilya Gridnev, Wanbin Zhang

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

An efficient nickel-catalyzed asymmetric hydrogenation of N-tBu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP* as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asymmetric hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.

Original languageEnglish
Pages (from-to)7329-7334
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number22
DOIs
Publication statusPublished - 2019 May 27

Keywords

  • amines
  • asymmetric catalysis
  • hydrogenation
  • nickel
  • reaction mechanisms

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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