Directed C-7 lithiation of 1-(2,2-diethylbutanoyl)indoles
1999; Elsevier BV; Volume: 55; Issue: 30 Linguagem: Inglês
10.1016/s0040-4020(99)00487-1
ISSN1464-5416
AutoresTsutomu Fukuda, Ryoichi Maeda, Masatomo Iwao,
Tópico(s)Chemical Reaction Mechanisms
ResumoDirected 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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