Switchable Reactivity of Acylated α, β-Dehydroamino Ester in the Friedel−Crafts Alkylation of Indoles by Changing the Lewis Acid
The Journal of Organic Chemistry2008Vol. 73(14), pp. 5654–5657
Citations Over TimeTop 10% of 2008 papers
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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