The Journal of Organic Chemistry

Reaction of ester enolates with nucleophiles. Stereocontrolled formation of ketone and aldehyde enolates

C Fehr, J Galindo

Index: Fehr, Charles; Galindo, Jose Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1828 - 1830

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Citation Number: 35

Abstract

Summary: Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles [RLi, RMgX, NaA1 (OC2H4OCH3), H2] to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively. This reaction is applied to the synthesis of y-damascone, a-damascone, p-safranal, and artemisia ketone.