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Synfacts 2008(11): 1149-1149
DOI: 10.1055/s-0028-1083483
DOI: 10.1055/s-0028-1083483
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2,5-Dihydro-(1H)-pyrrol-2-ones from Pyruvate, Aldehydes and Anilines
X. Li, H. Deng*, S. Luo*, J.-P. Cheng*
Institute of Chemistry, Chinese Academy of Sciences, Beijing and Nankai University, Tianjin, P. R. of China
Further Information
Publication History
Publication Date:
23 October 2008 (online)
Significance
Reported is a protocol for the synthesis of 2,5-dihydro-(1H)-pyrroles by a three-component condensation of ethyl pyruvate, aldehydes and anilines. The reaction is effectively promoted by a hydrogen-bonding catalyst, for example several ureas and organophosphoric acids, to give the products in good to excellent preparative yields. The screening of reaction conditions including catalysts, solvents, presence of dehydrating agents and influence of substrates was performed in detail. Unfortunately, attempts to use various chiral catalysts resulted in only moderate enantioinduction (ee ≤ 44%).