Generation, alkylation, and silylation of directed enolates formed by reaction of ketenes and organolithium reagents

LM Baigrie, D Lenoir, HR Seikaly…

Index: Baigrie, Lynn M.; Lenoir, Dieter; Seikaly, Hani R.; Tidwell, Thomas T. Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2105 - 2109

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Citation Number: 33

Abstract

Symmetrical ketenes R2C= C= 0 [&= t-Bu2 (l), Eh (21,(CH,),(3),(CH& (4)] were reacted with organolithium reagents R'Li to give directed enolates R, C= C (OLi) R'which were alkylated with Me1 or silylated with Me3SiC1. The silylation results for 2-4 were compared to those for reaction of ketones R2CHCO-n-Bu (16-18) with Me, SiCl and either i-PrzNLi, KH, or EgN. These latter conditions usually favored different regioisomers from the ketene route. ...