A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate

A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of α-trifluoromethylated γ-lactam compounds in good to exc...

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Bibliographic Details
Published in:Tetrahedron 2014-08, Vol.70 (31), p.4595-4601
Main Authors: Pei, Qing-Lan, Cui, Bao-Dong, Han, Wen-Yong, Wu, Zhi-Jun, Zhang, Xiao-Mei, Yuan, Wei-Cheng
Format: Article
Language:English
Subjects:
Brønsted acid
Ethyl trifluoropyruvate
Trifluoroacetic acid
β-Enamino esters
γ-Lactam compounds
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Summary:A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of α-trifluoromethylated γ-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.05.052