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Synfacts 2007(4): 0408-0408  
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

Contributor(s): Mark Lautens, Frédéric Ménard
T. Ohkuma*, K. Tsutsumi, N. Utsumi, N. Arai, R. Noyori, K. Murata
Hokkaido University, Sapporo, Kanto Chemical co., Saitama, Nagoya University, Japan
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Publication History

Publication Date:
23 March 2007 (online)

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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).