6533b826fe1ef96bd128464a
RESEARCH PRODUCT
Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters
Miguel CardaJuan MurgaFlorenci V. GonzálezEva FalomirJuan Alberto Marcosubject
Tertiary amineStereochemistryorganic chemicalsOrganic ChemistryPeriodic acidErythruloseBiochemistryAdductchemistry.chemical_compoundEnantiopure drugchemistryAldol reactionDrug Discoveryheterocyclic compoundsStereoselectivityHydratedescription
Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-α,β-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2000-01-01 | Tetrahedron |