Generation of the dianion of N-(trimethylsilyl) acetamide and reaction of the dianion with electrophilic reagents

PC Kuzma, LE Brown, TM Harris

Index: Kuzma, Peter C.; Brown, Lawrence E.; Harris, Thomas M. Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2015 - 2018

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Citation Number: 14

Abstract

1 sented a potential solution to the problem since the silyl groups can easily be removed by hydrolysis. Condensation with ketones occur in excellent yield, but other reactions including alkylations and, most important for us, acylations are only marginally succe~ sful.~ The enolate anion is thermally unstable; rearrangement to C-silylated derivatives competes with the desired condensation reactions in cases where the electrophile does not react ...