Tetrahedron

Conjugate addition of organolithium reagents to α, β-unsaturated carboxylic acids

MJ Aurell, LR Domingo, R Mestres, E Muñoz…

Index: Aurell, Maria Jose; Domingo, Luis Ramon; Mestres, Ramon; Munos, Elena; Zaragoza, Ramon Jose Tetrahedron, 1999 , vol. 55, # 3 p. 815 - 830

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Citation Number: 19

Abstract

Conjugate addition of primary, secondary, tertiary alkyl and phenyl lithium reagents to 2- alkenoic acids affords good yields of branched saturated carboxylic acids. Methyl groups at the α-and β-carbon of the 2-alkenoic acid decrease reactivity as acceptors, and foster deprotonation, respectively. The lithium enediolate resulting from the conjugate addition can react with electrophiles. PM3 calculations are in agreement with the substituent effects.