Variations in site of lithiation of N-[(2-(4-methoxyphenyl)ethyl)]pivalamide; use in ring substitution

Journal Article

Alshammari, M. B. . 2013

• Publication Work Type: Research
• Magazine \ Newspaper: Synlett
• Issue Number: 1
• Volume Number: 24
• Pages: 117–119

Publication Abstract

Lithiation of N-(2-(4-methoxyphenyl)ethyl)pivalamide at -20 to 0 °C with three mole 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.