Synthesis of 4-alkyl-1-benzhydryl-2-(methoxymethyl)azetidin3-ols by regio- and stereoselective alkylation of 1-benzhydryl-3-(N-alkyl)imino-2-(methoxymethyl)azetidine
(2002) Tetrahedron — Vol. 58, n° 14, p. 2763-2775 (2002)
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- 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.
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Salgado, A., Boeykens, M., Gauthier, C., Declercq, J.-P., & De Kimpe, N. (2002). Synthesis of 4-alkyl-1-benzhydryl-2-(methoxymethyl)azetidin3-ols by regio- and stereoselective alkylation of 1-benzhydryl-3-(N-alkyl)imino-2-(methoxymethyl)azetidine. Tetrahedron, 58(14), 2763-2775. https://doi.org/10.1016/S0040-4020(02)00178-3 (Original work published 2002)