Asymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir(III) Complexes Bearing a Chiral N-(2-Picolyl)sulfonamidato Ligand
Takuma Kawada, Kenya Yabushita, Toshihisa Yasuda, Takeshi Ohta, Takaaki Yajima, Kouichi Tanaka, Noriyuki Utsumi, Masahito Watanabe, Kunihiko Murata, Yoshihito Kayaki, Shigeki Kuwata* and Takeaki Katayama
*School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan,
Email: skuwata
fc.ritsumei.ac.jp
T. Kawada, K. Yabushita, T. Yasuda, T. Ohta, T. Yajima, K. Tanaka, N. Utsumi, M. Watanabe, K. Murata, Y. Kayaki, S. Kuwata, T. Katayama, J. Org. Chem., 2022, 87, 8458-8468.
DOI: 10.1021/acs.joc.2c00580
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Abstract
Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato catalyze a convenient asymmetric reductive amination of benzylic ketones using readily available β-amino alcohols as chiral aminating agents. The amino alcohol-derived chiral auxiliary was easily removed by mild periodic oxidants, leading to optically active primary β-arylamines without erosion of the optical purity.
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proposed mechanism
Key Words
reductive amination, primary amines, formic acid, periodic acid, dealkylation
ID: J42-Y2022
