Synfacts 2010(10): 1148-1148  
DOI: 10.1055/s-0030-1258644
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Hydrogenation of Imines

Contributor(s): Mark Lautens, Stephen G. Newman
J. Müslehiddinoğlu*, J. Li*, S. Tummala, R. Deshpande
Bristol-Myers Squibb Co., New Brunswick, USA
Further Information

Publication History

Publication Date:
22 September 2010 (online)

Significance

Chiral amines are of immense importance due to their ubiquity in pharmaceuticals. One process-friendly method to access chiral amines is by diastereoselective hydrogenation of imines derived from chiral amine auxiliaries. These hydrogenations are often done using highly reactive Raney nickel. On route to peliglitazar, a dual PPAR α/γ agonist, the authors encountered drawbacks on the use of Raney nickel on large scale. A Pd-Cu/C bimetallic catalyst was identified as a safe and economical alternative hydrogenation catalyst.