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Variations in Site of Lithiation of N-[2-(4-Methoxyphenyl)ethyl]pivalamide - Use in Ring Substitution
Journal article   Open access  Peer reviewed

Variations in Site of Lithiation of N-[2-(4-Methoxyphenyl)ethyl]pivalamide - Use in Ring Substitution

Keith Smith, Gamal A. El-Hiti and Mohammed B. Alshammari
Synlett, Vol.24(1), pp.117-119
01/01/2013
DOI: https://doi.org/10.1055/s-0032-1317859

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
Lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide at -20 to 0 degrees C with three equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.
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