Synthesis of 4-alkyl-1-benzhydryl-2-(methoxymethyl) azetidin-3-ols by regio-and stereoselective alkylation of 1-benzhydryl-3-(N-alkyl) imino-2-(methoxymethyl) …

…, M Boeykens, C Gauthier, JP Declercq, N De Kimpe

Index: Salgado, Antonio; Boeykens, Mark; Gauthier, Christine; Declercq, Jean-Paul; De Kimpe, Norbert Tetrahedron, 2002 , vol. 58, # 14 p. 2763 - 2775

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Citation Number: 18

Abstract

The regio-and stereoselective alkylation at the position C-4 of 1-alkyl-2-substituted azetidin- 3-ones was investigated. Imination of 1-benzhydryl-2-methoxymethylazetidin-3-one, followed by alkylation under kinetic conditions and final hydrolysis of the imino group, gave 4-alkyl-1-benzhydryl-2-methoxymethylazetidin-3-ones in which the susbstituents at C-2 and C-4 had the cis stereochemistry. The reduction of the carbonyl group afforded the ...