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Synfacts 2006(2): 0125-0125
DOI: 10.1055/s-2005-924775
DOI: 10.1055/s-2005-924775
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Ir-Catalyzed Asymmetric Ketimine Hydrogenation
C. Moessner, C. Bolm*
RWTH Aachen, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200602/lookinside/thumbnails/10.1055-s-2005-924775-1.jpg)
Significance
An Ir-catalyzed asymmetric hydrogenation of N-PMP ketimines using a chiral sulfoximinylphosphine as ligand gave good to excellent enantioselectivities and full conversion with 1 mol% catalyst loading within a few hours. A variety of aryl alkyl ketimines of different steric and electronic character were tolerated. More importantly, an E,Z-isomeric mixture of starting ketimines gave the products in excellent enantioselectivities. Lower Ir catalyst loading (0.1 mol%) was also able to achieve full conversion under increased H2 pressure without erosion of enantioselectivity. The N-PMP-protecting group can be easily removed under oxidative conditions (i.e. CAN).