The Use of Phosphite‐Type Ligands in the Ir‐Catalyzed Asymmetric Hydrogenation of Heterocyclic Compounds |
| |
| Authors: | Sergey E. Lyubimov Dmitry V. Ozolin Pavel Yu Ivanov Artem Melman Valeriya S. Velezheva Vadim A. Davankov |
| |
| Affiliation: | 1. Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia;2. Clarkson University, Potsdam, NY, USA |
| |
| Abstract: | A series of chiral phosphite‐type ligands was tested in asymmetric Ir‐catalyzed hydrogenation of quinolines and 2,4,5,6‐tetrahydro‐1H‐pyrazino(3,2,1‐j,k)carbazole. Hydrogenation of quinaldine hydrochloride provided superior enantioselectivity up to 65% ee compared to quinaldine free base. The ligands were tested for the first time in the asymmetric Ir‐Ircatalyzed hydrogenation of 2,4,5,6‐tetrahydro‐1H‐pyrazino(3,2,1‐j,k)carbazole yielding the antidepressant drug, pirlindole. Chirality 26:56–60, 2013. © 2013 Wiley Periodicals, Inc. |
| |
| Keywords: | asymmetric hydrogenation phosphites quinaldine hydrochloride pirlindole |
|
|
