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Synfacts 2008(8): 0842-0842  
DOI: 10.1055/s-2008-1077905
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Synthesis of α-Amino Boronate Esters

Contributor(s): Mark Lautens, Praew Thansandote
M. A. Beenen, C. An, J. A. Ellman*
University of California at Berkeley, USA
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

The asymmetric addition of (bispinacol)boron to various N-tert-butanesulfonyl ald­imines produces useful α-amino boronate esters in good yields and excellent diastereoselectivities. The reaction is not sensitive to steric or electronic changes on the aryl groups. The high synthetic utility of the products is demonstrated by the synthesis of the proteasome inhibitor bortezomib in five steps.