Synfacts 2010(3): 0322-0322  
DOI: 10.1055/s-0029-1219400
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Catalyzed Asymmetric Hydrogenation of N-Arylimines

Contributor(s): Mark Lautens, Chit Tsui
W. Li, G. Hou, M. Chang, X. Zhang*
The State University of New Jersey, Piscataway, USA
Further Information

Publication History

Publication Date:
18 February 2010 (online)

Significance

Chiral amines and their derivatives are of great significance in pharmaceutical, biological, and synthetic chemistry. Examples can be found in many drugs or drug candidates, such as Cinacalcet and NPS R-568. Catalytic asymmetric hydrogenation of imines is a powerful method for obtaining enantiomerically pure amine products due to its high efficiency, low catalyst loading, and atom economy. The authors report that high enantiomeric excesses were obtained in the asymmetric hydrogenation of various N-arylimines catalyzed by an iridium complex containing a highly rigid, electron-donating P-chiral bisphospholane ligand, DuanPhos. High turnover numbers (TONs) were achieved under mild reaction conditions.