Stereoselective synthesis of trifluoromethylated compounds: nucleophilic addition of formaldehyde N, N-dialkylhydrazones to trifluoromethyl ketones

…, R Fernández, JM Lassaletta

Index: Pareja, Carmen; Martin-Zamora, Eloisa; Fernandez, Rosario; Lassaletta, Jose M. Journal of Organic Chemistry, 1999 , vol. 64, # 24 p. 8846 - 8854

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Citation Number: 40

Abstract

The nucleophilic 1, 2-addition of formaldehyde N, N-dialkylhydrazones 1, 2, and 7-10 to trifluoromethyl ketones 3a-e takes place in the absence of any catalyst or promoter to afford a series of α-hydroxy-α-trifluoromethylhydrazones (4, 5, and 11-14) in good-to-excellent yields. From the several reagents studied, optimal results were achieved using 1- (methyleneamino) pyrrolidine (2) for the synthesis of racemic adducts and (S)-1-( ...