Organic Letters
Organic Letters
5 years ago

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles
Koji Yamada, Takumi Abe, Takuro Suzuki, Masahiro Anada, Shigeki Matsunaga
A novel indole-2,3-epoxide equivalent, 2-hydroxyindoline-3-triethylammonium bromide, was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nucleophiles. By taking advantage of the nucleophilic character of the oxygen of the 2-hydroxyindoline, the interrupted retro-Claisen and interrupted Feist–Bénary reactions with 1,3-dicarbonyl compounds were efficiently achieved.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01940

DOI: 10.1021/acs.orglett.7b01940

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