Tetrahedron

Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols

A Salgado, Y Dejaegher, G Verniest, M Boeykens…

Index: Salgado, Antonio; Dejaegher, Yves; Verniest, Guido; Boeykens, Mark; Gauthier, Christine; Lopin, Christelle; Tehrani, Kourosch Abbaspour; De Kimpe, Norbert Tetrahedron, 2003 , vol. 59, # 13 p. 2231 - 2239

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Citation Number: 19

Abstract

Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride- induced cyclization of the corresponding β-bromo-α, α-dimethoxyketimines, the resulting 3, 3- dimethoxyazetidines being hydrolyzed by acid. Imination of these 1, 2-disubstituted azetidin- 3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2, 4-and 2, 2-dialkylated compounds. Analytical samples of the major 2, 4- ...