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Synfacts 2009(6): 0648-0648  
DOI: 10.1055/s-0029-1217200
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ir-Catalyzed Enantioselective Hydrogenation of Trifluoromethyl Olefins

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
M. Engman, P. Cheruku, P. Tolstoy, J. Bergquist, S. F. Völker, P. G. Andersson*
Uppsala University, Sweden
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

In previous work, the authors have reported the first example of iridium-catalyzed asymmetric hydrogenation of vinyl fluorides (J. Am. Chem. Soc. 2007, 129, 4536). In the present study the authors report the first iridium-catalyzed asymmetric hydrogenation of simple trifluoromethyl alkenes with excellent yields and ee values using chiral N,P-ligands. Prior to this study, chiral Rh and Ru catalytic systems had been applied to hydrogenation of CF3-substituted olefins. However, in all cases a coordinating group near the substrate double bond was necessary to obtain high asymmetric induction.

Review: K. Iseki J. Fluorine Chem. 1994, 69, 5-6.