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RESEARCH PRODUCT
Stereoselective synthesis of syn-α-methyl-β-hydroxy esters
Florenci V. GonzálezEva FalomirJuan MurgaMiguel CardaJ. Alberto Marcosubject
chemistry.chemical_classificationKetoneStereochemistryOrganic ChemistryErythruloseCatalysisAdductInorganic Chemistrychemistry.chemical_compoundEnantiopure drugAldol reactionchemistryYield (chemistry)PropionateStereoselectivityPhysical and Theoretical Chemistrydescription
Abstract Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2- syn /1,3- syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O -formylated syn -α-methyl-β-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2000-08-01 | Tetrahedron: Asymmetry |