6533b858fe1ef96bd12b57dc
RESEARCH PRODUCT
ChemInform Abstract: Boron Aldol Additions with Erythrulose Derivatives: Dependence of Stereoselectivity on the Type of Protecting Group.
Encarnación CastilloMiguel CardaJuan MurgaEva FalomirFlorenci V. GonzálezJ. Alberto Marcosubject
chemistry.chemical_elementErythruloseGeneral MedicineMedicinal chemistryChloridechemistry.chemical_compoundchemistryAldol reactionReagentmedicineStereoselectivityBoronProtecting groupmedicine.drugdescription
Abstract Boron aldol additions of 1- O -silylated 3,4-di- O -benzyl- and 3,4-di- O -benzoyl- l -erythrulose and achiral aldehydes using dicyclohexylboron chloride have been investigated. The dibenzyl derivative gave syn/syn stereoisomers with high stereoselectivity, whereas the dibenzoyl derivative gave syn/anti stereoisomers. It is believed that, while the dibenzoyl erythrulose gives rise to the E enolate in the presence of dicyclohexylboron chloride, as usually observed with this reagent, only the Z enolate is formed in the case of the dibenzyl derivative.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-06-12 | ChemInform |