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Synfacts 2007(4): 0408-0408
DOI: 10.1055/s-2007-968342
DOI: 10.1055/s-2007-968342
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Hydrogenation of α-Chloro Aromatic Ketones
T. Ohkuma*, K. Tsutsumi, N. Utsumi, N. Arai, R. Noyori, K. Murata
Hokkaido University, Sapporo, Kanto Chemical co., Saitama, Nagoya University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. März 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968342-1.jpg)
Significance
The Ru(II)-precatalyst system (S,S)-2 was demonstrated to be efficient for the hydrogenation of α-chloro aromatic ketones. Chiral α-chloro alcohols 3 are synthetically useful, but no genenal and reliable catalyst system has been reported for base-sensitive ketones like 1. The non-basic reaction conditions allowed the reaction to yield phenol 3c without protection. Substrates bearing an EWG on the aromatic ring showed slightly diminished, but still excellent enantioselectivity (3e and 3f, 93% and 94% ee, respectively).