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Synfacts 2009(7): 0769-0769  
DOI: 10.1055/s-0029-1217293
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Elemental Copper Catalyzed Stereoselective Aminobromination

Contributor(s): Hisashi Yamamoto, Zhi Li
Z.-G. Chen, J.-F. Wei*, R.-T. Li, X.-Y. Shi, P.-F. Zhao
Shaanxi Normal University and Peking University, Beijing, P. R. of China
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Publikationsdatum:
22. Juni 2009 (online)

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Significance

Stereoselective aminohalogenation is a challenging problem for organic synthesis. In this report, a convenient procedure for ­aminobromination of α,β-unsaturated ketones catalyzed by copper powder is described. The method can provide the aminobromination products in almost quantitative yields and complete anti-selectivity with only 1 mol% catalyst loading under aerial conditions. Copper metal was also proven to be more efficient than CuI in this ­transformation.