Tetrahedron

Directed C-7 lithiation of 1-(2, 2-diethylbutanoyl) indoles

T Fukuda, R Maeda, M Iwao

Index: Fukuda, Tsutomu; Maeda, Ryoichi; Iwao, Masatomo Tetrahedron, 1999 , vol. 55, # 30 p. 9151 - 9162

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Citation Number: 24

Abstract

Directed lithiation of 1-acylindole derivatives was investigated. It was discovered that a bulky 2, 2-diethylbutanoyl (DEB) group could promote unusual C-7 lithiation. Especially in the case of 3-substituted 1-(DEB) indoles, selective C-7 lithiation was achieved in a synthetically useful level. The DEB group was readily removed by H2O/tert-BuOK/THF system after functionalization at C-7. This, therefore, allows easy generation of 3, 7-disubstituted indole ...