Directed metalation of aromatic aldimines with lithium 2, 2, 6, 6-tetramethylpiperidide

LA Flippin, JM Muchowski…

Index: Flippin, Lee A.; Muchowski, Joseph M.; Carter, David S. Journal of Organic Chemistry, 1993 , vol. 58, # 9 p. 2463 - 2467

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Citation Number: 23

Abstract

A synthetic method for directed metalation of protected aromatic aldehydes that is both convenient and broadly applicable has proved elusive despite several impressive efforts toward this goal. In the course of their seminal investigations of directed metalation of aromatic aldimines Ziegler and Fowler'demonstrated that 3, 4-(methylenedi0xy) benzaldehyde cyclohexylimine can be efficiently lithiated on the aromatic ring at C (2) with ...