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

Keith Smith, Gamal El-Hiti, Mohammed Alshammari
2012 Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry  
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.
doi:10.1055/s-0032-1317859 fatcat:yersqae5w5gavjph25zp3azkbi