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Synfacts 2006(1): 0049-0049  
DOI: 10.1055/s-2005-921671
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Unnatural Amino Acids via Reductive C-C Bond Forming Hydrogenation

Contributor(s): Mark Lautens, Andrew Martins
J.-R. Kong, C.-W. Cho, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

A variety of alkynes in the presence of enantiopure tert-butylsulfinimines undergo Rh(I)-catalyzed reductive C-C bond forming hydrogenation to afford N-sulfinyl-α-amino acids in good to excellent yield and with very good diastereoselection. Various alkyne substituents are tolerated, including protected amines, and protected or unprotected alcohols.