The Journal of Organic Chemistry

An alternative route to 2-substituted indoles via N-aminal-directed lithiation

AR Katritzky, P Lue, YX Chen

Index: Katritzky, Alan R.; Lue, Ping; Chen, Ya-Xiong Journal of Organic Chemistry, 1990 , vol. 55, # 11 p. 3688 - 3691

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Citation Number: 31

Abstract

The directing effect of (dialky1amino) methyl (aminal) groups in carbocyclic metalation chemistry is well known.'Recently, we have found that aminal groups can also be successfully employed as protecting groups for the NH of heterocyclic compounds and as directing groups for the subsequent lithiation of heterocyclic compounds. This methodology works well for a variety of NH-containing heterocycles, including carbazole, imidazole, ...