Post-M etalation Structural Insights into the Use of Alkali-Metal-Mediated Zincation for Directed ortho-Metalation of a Tertiary Aromatic Amide

摘要

Introduced in 1999 by Kondo etal.,lithium di-tert-butyl-tetramethylpiperidinozincate (LiTMP-zincate) is a highly chemoselective base for directed ortho-metalation (DoM) of alkyl benzoates,alkyl benzamides,and related aza-aromatics.This important reagent is but one of a growing number of alkali-metal zincate compounds that are attracting much attention from synthetic chemists in respect of their often special reactivities/selectivities,and in certain cases,catalytic action towards organic substrates.