6533b827fe1ef96bd1285c6b
RESEARCH PRODUCT
Enantioselective Synthesis of Unsymmetrical Benzoins from (S)-Mandelic Acid Enolate and Aromatic Aldehydes.
Gonzalo BlayIsabel FernándezJosé R. PedroBelen Monjesubject
Chemistryorganic chemicalsOrganic ChemistryEnantioselective synthesischemistry.chemical_elementGeneral MedicineOptically activeMandelic acidBiochemistrychemistry.chemical_compoundAldol reactionDrug Discoverypolycyclic compoundsOrganic chemistryMoietyLithiumEnantiomerOxidative decarboxylationdescription
The reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with aromatic aldehydes proceeds readily to give the corresponding aldol products in good yields and diastereoselectivities. Subsequent hydroxyl protection, basic hydrolysis of the dioxolanone, oxidative decarboxylation of the α-hydroxyacid moiety, and hydroxyl deprotection provides chiral unsymmetrical benzoins with high enantiomeric excesses.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-10-01 | ChemInform |