Synthesis and reactions of N-protected 2-lithiated pyrroles and indoles. The tert-butoxycarbonyl substituent as a protecting group

I Hasan, ER Marinelli, LCC Lin…

文献索引：Hasan, Iltifat; Marinelli, Edmund R.; Lin, Li-Ching Chang; Fowler, Frank W.; Levy, Alan B. Journal of Organic Chemistry, 1981 , vol. 46, # 1 p. 157 - 164

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被引用次数: 149

摘要

N-(tert-Butoxycarbony1) pyrrole and N-(tert-butoxycarbony1) indole have been prepared and lithiated at the 2-position with lithium 2, 2, 6, 6-tetramethylpiperidide and tert- butyllithium, respectively. These lithium reagents react with a variety of electrophiles to give the 2-substituted N-(tert-butoxycarbony1) pyrroles and N-(tert-butoxycarbony1) indoles. The N-(tert-butoxycarbonyl) substituent may be removed rapidly and in high yield from the ...