Diastereoselective Hydrogenation of Substituted Quinolines

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%.