Selective C-3 and C-2 lithiation of 1-(2,2-diethylbutanoyl)indole

Authors
Fukuda, T Mine, Y Iwao, M
Citation
T. Fukuda et al., Selective C-3 and C-2 lithiation of 1-(2,2-diethylbutanoyl)indole, TETRAHEDRON, 57(6), 2001, pp. 975-979
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
6
Year of publication
2001
Pages
975 - 979
Database
ISI
SICI code
0040-4020(20010204)57:6<975:SCACLO>2.0.ZU;2-D
Abstract
1-(2,2-Diethylbutanoyl)indole (1) can be lithiated regioselectively at C-3 by treatment with sec-BuLi-PMDTA in hexane at -78 degreesC, In contrast, 1 is lithiated at C-2 with sec-BuLi-tert-BuOK in THF at -78 degreesC. The gen erated C-3 and C-2 lithio species were trapped with a variety of electrophi les to give the corresponding substitution products. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.