Synfacts 2010(5): 0572-0572  
DOI: 10.1055/s-0029-1219640
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Hydrogenation of Substituted Quinolines

Contributor(s): Hisashi Yamamoto, Jiajing Tan
M. Heitbaum, R. Fröhlich, F. Glorius*
Universität Münster, Germany
Further Information

Publication History

Publication Date:
22 April 2010 (online)

Significance

The authors reported a two-step, efficient stereoselective hydrogenation of auxiliary-substituted quinolines to enantiomerically pure decahydroquinolines. In the first step, 5,6,7,8-­tetrahydroquinolines were obtained with dia­stereomeric ratios up to 89:11 by hydrogenation of 2-oxazolidinone-substituted quinolines under Adam’s catalyst (PtO2). In the second step, the decahydroquinolines with four new stereocenters were obtained with enantiomeric excesses up to 99%.