Synthesis of 1-alkyl-2-(trifluoromethyl) azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl) amines via intermediate azetidinium salts

…, M D'hooghe, G Verniest, TA Dang Thi…

Index: Kenis, Sara; D'Hooghe, Matthias; Verniest, Guido; Dang Thi, Tuyet Anh; Pham The, Chinh; Van Nguyen, Tuyen; De Kimpe, Norbert Journal of Organic Chemistry, 2012 ,  vol. 77,  # 14  p. 5982 - 5992

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Citation Number: 26

Abstract

A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl) azetidines as a new class of constrained azaheterocycles was developed starting from ethyl 4, 4, 4- trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the ...