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Synfacts 2010(12): 1372-1372  
DOI: 10.1055/s-0030-1258902
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Catalyzed Asymmetric Hydrogenation of Unprotected β-Enamine Esters

Contributor(s): Hisashi Yamamoto, Jiajing Tan
G. Hou, W. Li, M. Ma, X. Zhang, X. Zhang*
Rutgers, The State University of New Jersey, Piscataway, USA
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

Expanding their work on the asymmetric hydrogenation methodology, this work demonstrated a highly efficient enantioselective hydrogenation of unprotected β-enamine esters catalyzed by an iridium (S,S)-f-binaphane complex. The free β-enamine acids were obtained in excellent yields and enantioselectivities (for asymmetric hydrogenation of unprotected NH imines, see: G. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. O’Shea, C.-y. Chen, I. W. Davies, X. Zhang J. Am. Chem. Soc. 2009, 131, 9882).