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Paper | Special issue | Vol 97, No. 2, 2018, pp.968-997
Published online, 6th April, 2018
DOI: 10.3987/COM-18-S(T)77
Lithiation of 1-Alkoxyindole Derivatives

Kyoko Nakagawa (Goto), Tetsuya Kobayashi, Toshiya Kawasaki, and Masanori Somei*

*Noto Marine Laboratory, Institute of Nature and Environmental Technology, Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, 56-7 Matsuhidai, Matsudo-shi, Chiba 270-2214, Japan

Abstract

Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.