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Communication | Regular issue | Vol 29, No. 9, 1989, pp.1661-1662
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5079
C3-Acylation of Indoles via C3-Lithiation Directed by the C2-Carboxyl Group

Yuusaku Yokoyama, Masahiko Uchida, and Yasuoki Murakami*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


N-Protected indole-2-carboxylic acid (1) was lithiated at the 3-position using sec-BuLi in the presence of an additive (HMPA) in THF, and then acylated at that position regioselectively by subsequent treatment with ester or DMF in moderate yields.