The Journal of Organic Chemistry

Lithiation of heterocycles directed by. alpha.-amino alkoxides

DL Comins, MO Killpack

Index: Comins, Daniel L.; Killpack, Michael O. Journal of Organic Chemistry, 1987 , vol. 52, # 1 p. 104 - 109

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Citation Number: 98

Abstract

The addition of heterocyclic aromatic aldehydes to certain lithium dialkylamides gave a- amino alkoxides that were ring-lithiated with butyllithium. Alkylation and hydrolysis provided ring-substituted heterocyclic aromatic aldehydes via a one-pot reaction. The metalation of a- amino alkoxides derived from thiophenecarboxaldehydes, furaldehydes, N- methylpyrrolecarboxaldehydes, and indolecarboxaldehydes was examined. The ...

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