Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Shuang Gao
  • Weijun Zeng
  • Shan Xin
  • Qin Yin
  • Xumu Zhang

Detail(s)

Original languageEnglish
Pages (from-to)2024-2027
Journal / PublicationJournal of the American Chemical Society
Volume140
Issue number6
Publication statusPublished - 14 Feb 2018
Externally publishedYes

Abstract

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented. © 2018 American Chemical Society.

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Citation Format(s)

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2. / Tan, Xuefeng; Gao, Shuang; Zeng, Weijun et al.
In: Journal of the American Chemical Society, Vol. 140, No. 6, 14.02.2018, p. 2024-2027.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review