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

doi:10.1055/s-0029-1217722

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Synlett 2009(14): 2242-2244
DOI: 10.1055/s-0029-1217722

LETTER

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

Keith Smith*, Gamal A. El-Hiti, Amany S. HegazySchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
Fax: +44(2920)870600; e-Mail: smithk13@cardiff.ac.uk;

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Publication History

Received 21 May 2009
Publication Date:
03 August 2009 (eFirst)

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Abstract

Directed lithiation of N-(2-methoxybenzyl)pivalamide with two mole equivalents of t-BuLi in anhydrous THF at -78 ˚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.

Key words

N-(2-methoxybenzyl)pivalamide - directed lithiation - synthesis - dilithium intermediate - electrophile