Tetrahedron p. 9151 - 9162 (1999)
Update date:2022-08-05
Topics:
Fukuda, Tsutomu
Maeda, Ryoichi
Iwao, Masatomo
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 derivatives which are not readily available by conventional methodologies.
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