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  • 1
    Electronic Resource
    Electronic Resource
    Stereochemie der Dehydratisierung und Halogenierung der αRS*- und αS*-Isomere von 3-(α-Hydroxybenzyl)-1,4-diphenyl-2-azetidinonen (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1162-1168 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Stereochemistry of Dehydration and Halogenation of αR* and αS* Isomeric 3-(α-Hydroxybenzyl)-1,4-diphenyl-2-azetidinonesDehydration with p-tosyl chloride in pyridine starting with the αR* isomers of the title compounds 3 results in formation of (E)-3-arylmethylene-β-lactams 4. (Z)-4 is obtained by starting with αS* isomeric 3. Halogenation of αS*-3 with thionyl chloride in chloroform yields αR* halogeno compounds 6 by inversion at C-α, and dehydrohalogenation of 6 by amines results in the specific formation of (E)-4.
    Notes: Die Dehydratisierung mit p-Tosylchlorid in Pyridin ergibt aus den αR*-Isomeren der Titelverbindungen 3 nur die (E)-3-Arylmethylen-β-lactame 4 und ausgehend von den αS*-Isomeren von 3 nur die (Z)-Isomeren 4. Aus αS*-3 werden durch Halogenierung mit Thionylchlorid in Chloroform unter Inversion an C-α die αR*-Halogenverbindungen 6 erhalten, deren Dehydrochlorierung spezifisch zu (E)-4 führt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830708
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Darstellung und Stereochemie von 3-(α-Hydroxybenzyl)-1,4-diphenyl-2-azetidinonen (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1152-1161 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Stereochemistry of 3-(α-Hydroxybenzyl)-14-diphenyl-2-azetidinonesAldol reaction between benzaldehydes and 1,4-diphenyl-2-azetidinones 1 catalyzed by lithium diisopropylamide results in formation of the title compounds. The reactions give satisfactory yields and high diastereoselectivity at three centres in forming the αS*,3S*,4R* configuration. The same configuration is preponderant if acetaldehyde is reacted with 1.
    Notes: Die Aldol-Addition von Benzaldehyden an 1,4-Diphenyl-2-azetidinone 1 in Gegenwart von Lithium-diisopropylamid führt in guten Ausbeuten und mit hoher Diastereoselektivität an drei Zentren zu den Titelverbindungen mit αS*,3S*,4R*-Konfiguration. Die gleiche Konfiguration wird bei Umsetzungen von 1 mit Acetaldehyd bevorzugt gebildet.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830707
    Library Location Call Number Volume/Issue/Year Availability
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    Paper (German National Licenses)
    Fulltext
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