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  • 1
    ISSN: 0947-3440
    Schlagwort(e): Photochemistry ; Ring opening reactions ; Oxetanes ; Reductions ; Alcohols ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The title compounds 7 were prepared in situ by deprotection of the corresponding pivaloyl-substituted oxetanes 3 with lithium aluminium hydride in tetrahydrofuran. under these conditions a reductive ring opening at c-2 (hydrodealkoxylation) occurred which was initiated by a nucleophilic hydride attack and which yielded the triols 8 (64-85%). the facility of the reaction and its high regioselectivity can be explained by the directing ability of the hydroxy group at the aromatic substituent. The reaction proceeds stereospecifically, as shown by deuterium labelling experiments. The prerequisite 2-(2-pivaloyloxyphenyl)-3-[(trimethylsilyl)oxy]oxetanes 3 were prepared by the Paternò-Büchi reaction of the protected salicylaldehyde 1 and various silyl enol ethers 2. The 2-hydroxyphenyl substituent at the C-3 position of oxetane 6 directed the hydride attack to the C-4 position and yielded the triol 10 in 85% yield.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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  • 2
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2265-2267 
    ISSN: 0947-3440
    Schlagwort(e): Antibiotics ; Amino acids ; Photochemistry ; Oxetanes ; Protective groups ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Paternò-Büchi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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  • 3
    ISSN: 0947-3440
    Schlagwort(e): Photochemistry ; Synthetic methods ; Oxetanes ; Diols ; Amino alcohols ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The preparation of 3-heteroatom-substituted oxetanes by the Paternò-Büchi reaction, and their application in synthesis are reviewed. 3-Oxetanols and 3-aminooxetanes are the two most important oxetanes in this respect. By tuning the electronic properties of the enol and enamine substrates, a successful photocycloaddition to carbonyl compounds, with high yield, is possible. Since the oxetane formation proceeds stereoselectively, diastereomerically pure products are readily accessible, which can then be used in further transformations. To this end, regioselective ring-opening reactions have been developed, some of which will be discussed in this account.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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