6533b839fe1ef96bd12a5a1b
RESEARCH PRODUCT
Conjugate addition of organolithium reagents to α,β-unsaturated carboxylic acids
Ramón J. ZaragozáRamon MestresMaría José AurellLuis R. DomingoElena Muñozsubject
chemistry.chemical_classificationOrganic ChemistrySubstituentchemistry.chemical_elementBiochemistryMedicinal chemistrychemistry.chemical_compoundDeprotonationchemistryReagentDrug DiscoveryElectrophileLithiumReactivity (chemistry)AlkylConjugatedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-01-01 | Tetrahedron |