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RESEARCH PRODUCT
Efficient Addition of Acid Enediolates to Epoxides
Natalia OrtúzarRichard WincewiczMercedes TorresSalvador GilMargarita Parrasubject
Alternative methodschemistry.chemical_compoundNucleophilic additionchemistryOrganic ChemistryEpoxideLithium chlorideRegioselectivityOrganic chemistryAmine gas treatingLewis acids and basesPhysical and Theoretical Chemistrydescription
We report new conditions to facilitate the addition of dianions of carboxylic acids to epoxides as an alternative method to the use of aluminum enolates. These conditions require the use of a sub-stoichiometric (10%) amount of amine for dianion generation and the previous activation of the epoxide with LiCl. Other Lewis acids have been shown to be less effective. Yields are good but only low diastereoselectivity is attained, which has not been controlled despite attempts at optimization. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-05-01 | European Journal of Organic Chemistry |