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  • Title: Switchable reactivity of acylated alpha, beta-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid.
    Author: Angelini E, Balsamini C, Bartoccini F, Lucarini S, Piersanti G.
    Journal: J Org Chem; 2008 Jul 18; 73(14):5654-7. PubMed ID: 18558761.
    Abstract:
    Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.
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