6533b833fe1ef96bd129bfd1
RESEARCH PRODUCT
Boron aldol additions with erythrulose derivatives: dependence of stereoselectivity on the type of protecting group
Eva FalomirMiguel CardaEncarnación CastilloFlorenci V. GonzálezJuan MurgaJ. Alberto Marcosubject
ChemistryStereochemistryOrganic Chemistrychemistry.chemical_elementErythruloseBiochemistryChloridechemistry.chemical_compoundAldol reactionReagentDrug DiscoverymedicineStereoselectivityProtecting groupBoronmedicine.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 |
|---|---|---|---|---|
| 1999-09-01 | Tetrahedron Letters |