Methodology for the efficient synthesis of 3,4-differentially substituted indoles. Fluoride ion-induced elimination-addition reaction of 1-triisopropylsilylgramine methiodides

Article abstract of DOI:10.1016/00404-0399(50)1197P-

1-Triisopropylsilylgramine methiodide reacted smoothly with a variety of nucleophiles in the presence of tetrabutylammonium fluoride to give 3-substituted indoles. The 3,4-disubstituted indoles were efficiently synthesized by sequential use of 4-selective lithiation of 1-triisopropylsilylgramine and this new substitution reaction.