A. Salgado, M. Boeykens, C. Gauthier
Apr 1, 2002
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0
Influential Citations
17
Citations
Journal
Tetrahedron
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 corresponding 4-alkyl-1-benzhydryl-2-methoxymethylazetidin-3-ols. The structure and the stereochemistry of the azetidinols were confirmed by single crystal X-ray diffraction analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.