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Title
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Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols
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Author
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Abstract
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| Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-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-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved. |
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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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2003
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/S0040-4020(03)00241-2
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Volume/pages
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59
:13
(2003)
, p. 2231-2239
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ISI
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000181731500005
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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