Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Peng Yang
  • Li Hui Lim
  • Pratanphorn Chuanprasit
  • Hajime Hirao
  • Jianrong(Steve) Zhou

Detail(s)

Original languageEnglish
Pages (from-to)12083-12087
Journal / PublicationAngewandte Chemie - International Edition
Volume55
Issue number39
Online published30 Aug 2016
Publication statusPublished - 19 Sep 2016
Externally publishedYes

Abstract

An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one-pot synthesis of tetrahydroquinoxalines was also developed starting directly from α-ketoaldehydes and 1,2-diaminobenzene. Formic acid was used as a safe and economic surrogate for high-pressure hydrogen gas. Strongly σ-donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.

Research Area(s)

  • chiral alkylamines, nickel, reductive amination, synthetic methods, transfer hydrogenation

Citation Format(s)

Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. / Yang, Peng; Lim, Li Hui; Chuanprasit, Pratanphorn et al.

In: Angewandte Chemie - International Edition, Vol. 55, No. 39, 19.09.2016, p. 12083-12087.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review