Synthesis of (E)??1??Propenyl Ketones from Carboxylic Esters and Carboxamides by Use of Mixed Organolithium??Magnesium Reagents. Synthesis of α??Damascone, β …

C Fehr, J Galindo

Index: Fehr, Charles; Galindo, Jose Helvetica Chimica Acta, 1986 , vol. 69, p. 228 - 235

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Citation Number: 34

Abstract

Abstract The novel reagents formed by combination of allylmagnesium chloride and a strong non-nucleophilic lithium base (LiNR 2) convert non-or slowly enolizable carboxylic esters or carboxamides into 2-propenyl ketones which are protected from further reaction by their in situ conversion into enolates. This modified Grignard reaction is applied to efficient syntheses of α-damascone, β-damascone, β-damascenone, and various other (E)-1- ...