Convenient and efficient decarboxylative aldol reaction of malonic acid half esters with trifluoromethyl ketones

A convenient and efficient decarboxylative ketone aldol condensation of malonic acid half esters was reported. In the presence of catalytic amount of triethylamine, a series of aromatic and alkyl trifluoromethyl ketones were transformed into the desired adducts in 61–99% yields. In a preliminary exp...

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Veröffentlicht in:Tetrahedron letters 2012-04, Vol.53 (16), p.2117-2120
Hauptverfasser: Li, Xiao-Juan, Xiong, Heng-Ying, Hua, Ming-Qing, Nie, Jing, Zheng, Yan, Ma, Jun-An
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Sprache:eng
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Zusammenfassung:A convenient and efficient decarboxylative ketone aldol condensation of malonic acid half esters was reported. In the presence of catalytic amount of triethylamine, a series of aromatic and alkyl trifluoromethyl ketones were transformed into the desired adducts in 61–99% yields. In a preliminary experiment, a moderate stereoselectivity was obtained. Direct reduction of the aldol product with LiAlH4 afforded trifluoromethylated 1,3-diol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.02.053