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

Journal Article

Alshammari, M. B. . 2013

• نوع عمل المنشور: Research
• المجلة \ الصحيفة: Synlett
• رقم العدد: 1
• رقم الإصدار السنوي: 24
• الصفحات: 117–119

مستخلص المنشور

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.