Preparation of. alpha.-Methylene and. alpha.-Ethylidene. beta.-Lactams via the Ester Enolate-Imine Condensation Using. beta.-(Dialkylamino) Esters as Starting …

…, G Esteban, Y Martin-Cantalejo, J Plumet…

Index: Alcaide, Benito; Esteban, Gemma; Martin-Cantalejo, Yolanda; Plumet, Joaquin; Rodriguez-Lopez, Julian; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 26 p. 7994 - 8002

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Citation Number: 32

Abstract

A new, simple procedure for the preparation of appropriately substituted a-methylene and a- ethylidene p-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 34dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate a-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced a-[(dialkylamino) alkyl] p-lactams stereoselectively and in ...

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