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Paper | Special issue | Vol 74, No. 1, 2007, pp.461-472
Published online, 21st September, 2007
DOI: 10.3987/COM-07-S(W)25
Preparation of Ethylene Glycol Adducts at 2,3-Positions of Indoles with Hypervalent Iodine

Naoki Okada, Kaori Misawa, Mariko Kitajima, and Hiromitsu Takayama*

*Laboratory of Molecular Structure and Biological Function, Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

An efficient method for protection-deprotection of the 2,3-bond of indoles was developed. Treatment of various indole derivatives with hypervalent iodine-ethylene glycol in the presence of ammonium chloride provided 2,3-ethylene glycol bridged adducts in excellent yields. The adducts, which possessed a masked form of pyrrole moiety in the indole nucleus, could be converted back to the mother indoles under mild reductive conditions.