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Synfacts 2009(12): 1361-1361  
DOI: 10.1055/s-0029-1218319
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Asymmetric Hydrogenation

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
D. A. Rankic, J. M. Hopkins, M. Parvez, B. A. Keay*
University of Calgary, Canada
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

In this paper the authors report the synthesis and resolution of 3,3′-disubstituted xylBINAP derivatives and their application as ligands for rhodium-catalyzed asymmetric hydrogenation of dehydroamino acids and enamides. Under optimized conditions ligand 5, bearing chiral moieties at the 3,3′-positions, demonstrated excellent ­results for hydrogenation of methyl N-acetamido cinnamic acid (>99% ee).