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Unexpected Variations in Sites of Lithiation of N-(2-Methoxybenzyl)-pivalamide
Journal article   Peer reviewed

Unexpected Variations in Sites of Lithiation of N-(2-Methoxybenzyl)-pivalamide

Keith Smith, Gamal A. El-Hiti and Amany S. Hegazy
Synlett, Vol.2009(14), pp.2242-2244
01/09/2009
DOI: https://doi.org/10.1055/s-0029-1217722

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
Directed lithiation of N-(2-methoxybenzyl)pivalamide with two mole equivalents of t-BuLi in anhydrous THF at -78 degrees C followed by reactions with various electrophiles gave ring substitution, but ortho to the methoxy group rather than ortho to the pivaloylaminomethyl group, which was unexpected in view of earlier results reported with n-BuLi.

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