6533b82cfe1ef96bd128f437

RESEARCH PRODUCT

Lithium enediolates and dienediolates of carboxylic acids in synthesis: Alkylation with secondary halides

Eva M. BrunSalvador GilMargarita ParraRamon Mestres

subject

chemistry.chemical_classificationDouble bondChemistryOrganic Chemistrychemistry.chemical_elementHalideAlkylationBiochemistryElimination reactionDrug DiscoveryOrganic chemistrylipids (amino acids peptides and proteins)Rather poorStereoselectivityLithium

description

Abstract High yields in the alkylation of dianions of α,β-unsaturated carboxylic acids with secondary halides can be obtained despite elimination reactions occurring. α-Regioselectivity for the alkylation of but-2-enoic acids ( 1–4 ) is seldom obtained. Although double bond stereoselectivity is higher than 99% for γ-alkylated products, stereoselectivity is rather poor for most of the α-alkylated products.

https://doi.org/10.1016/s0040-4020(98)00957-0