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

• Published in: Angewandte Chemie International Edition Vol. 59; no. 13; pp. 5321 - 5325
• Main Authors: Hu, Le' an, Zhang, Yao, Zhang, Qing‐Wen, Yin, Qin, Zhang, Xumu
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 23.03.2020
• Edition: International ed. in English
• Subjects: Amination; amines; Ammonium; Ammonium salts; Asymmetry; Bioactive compounds; diaryl ketones; homogeneous catalysis; Ketones; reductive amination; Ruthenium; Salts
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201915459

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. OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity.