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Synfacts 2007(9): 0958-0958  
DOI: 10.1055/s-2007-968863
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective C-C Bond-Forming Hydrogenation via Rhodium

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
E. Skucas, J. R. Kong, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

The authors report the first highly enantioselective catalytic vinylation of N-arylsulfonyl aldimines via an interesting rhodium-mediated C-C bond-forming hydrogenation. This study closely follows previous work from the same lab involving reductive coupling of acetylene to aldehydes and α-ketoesters (J. Am. Chem. Soc. 2006, 128, 16040). While a wide array of para- and meta-substituted aryl substrates gave excellent results, benzaldimines possessing ortho substitution did not react efficiently.