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Synfacts 2010(6): 0691-0691
DOI: 10.1055/s-0029-1219862
DOI: 10.1055/s-0029-1219862
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Three-Component Reactions: Access to Furan Derivatives
Y. Zhu, C. Zhai, L. Yang, W. Hu*
East China Normal University, Shanghai, P. R. of China
Further Information
Publication History
Publication Date:
20 May 2010 (online)
Significance
The authors previously reported that alcoholic oxonium ylides generated in situ from diazo compounds and alcohols in the presence of Rh2(OAc)4 can be trapped by aldehydes and imines. In this report, copper complexes were shown to be superior catalysts (in terms of yield and cost) in the stereoselective three-component reactions of aryl diazoacetates, alcohols, and chalcones for constructing γ-hydroxy ketone derivatives 1. Good yields and excellent syn/anti selectivities were achieved with Cu(OTf)2. Furthermore, the reaction can be scaled up to multigram quantities by using cheaper CuSO4 as catalyst.