4.8 Article

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 13, Pages 5321-5325

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915459

Keywords

amines; diaryl ketones; homogeneous catalysis; reductive amination; ruthenium

Funding

  1. National Natural Science Foundation of China [21801119]
  2. Shenzhen Science and Technology Innovation Committee [JCYJ20170817110055425, KQTD20150717103157174]
  3. Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]

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A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93->99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

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