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  • 1
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Friedel-Crafts Acylation of N-Phthaloyl-Substituted Arylalanyl and Homophenylalanyl ChloridesN-Phthaloyl-protected arylalanyl and homophenylalanyl chlorides 5 are acylated intramolecularly to 2-phtahlimido-1-indanones 6 and -1-tetralone (6d) with AlCl3 (two-fold molar amounts) or catalytic amounts of FeCl3. The cycloacylation to the tetralone 6d with AlCl3 or FeCl3 proceeds without racemisation in very good yields, whereas the cycloacylation to the indanone 6a with FeCl3 gives rise to racemisation. Mixed anhydrides 11 of N-phthaloyl-α-amino acids and trifluoromethanesulfonate were prepared from the N-phthaloylamino acid chlorides and silver triflate. Acylation of arenes 12 with 11a as well as cycloaddition of (S)-O-methyl-N-phthaloyltyrosine triflate [(S)-11e] can be achieved without racemisation and without a catalyst.
    Notes: Die intramolekulare Acylierung von N-Phthaloyl-geschützten Aryl- und Homophenylalanychloriden 5 mit zweifach molaren Mengen AlCl3 oder katalytischen Mengen FeCl3 führt zu 2-Phthal-imido-l-indanonen 6 bzw. -1-tetralon (6d). Während die Cyclo-acylierung zum Tetralon 6d mit AlCl3 und mit FeCl3 racemisierungsfrei mit sehr guten Ausbeuten abläuft, erfolgt die Bildung des Indanons 6a mit FeCl3 unter Racemisierung. N-Phthaloyl-geschützte α-Aminosäurechloride bilden mit Silber-trifluormethansulfonat gemischte Anhydride (z.B. 11a), die ohne Verwendung eines Katalysators racemisierungsfrei cyclisieren (s. z.B. 6e).
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
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