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Synfacts 2006(8): 0822-0822  
DOI: 10.1055/s-2006-941946
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Asymmetric Hydrogenation of Quinolines

Contributor(s): Mark Lautens, Yann Béthuel
M. T. Reetz*, X. Li
Max-Planck-Institut für Kohlenforschung, Mülheim, Germany
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

The authors have expanded the reaction scope for their BINOL-derived diphosphonite ligands initially developed in 1998 (Chem. Commun. 1998, 2077-2078) to the iridium-catalyzed asymmetric hydrogenation of quinolines. ­Excellent conversion and enantioselectivity have been obtained. This method represents a complement to the pre-existing literature in iridium-catalyzed hydrogenations of quinolines by Zhou who used (R)-MeO-Biphep or a ferrocenyloxazoline-derived P,N-ligand (J. Am. Chem. Soc. 2003, 125, 10536-10537; Adv. Synth. Catal. 2004, 346, 909-912) and Chan who described chiral dipyridyl­phosphane ligands or H8-BINAPO (Chem. Commun. 2005, 1390-1392; Adv. Synth. Catal. 2005, 347, 1755-1758).