6533b85efe1ef96bd12bf3e1
RESEARCH PRODUCT
Highly Diastereoselective Michael Reaction of (S)‐Mandelic Acid Enolate. Chiral Benzoyl Carbanion Equivalent Through an Oxidative Decarboxylation of α‐Hydroxyacids.
Gonzalo BlayIsabel FernándezRafael RuizBelen MonjeJosé R. Pedrosubject
Addition reactionOrganic ChemistryAcetalGeneral MedicineMandelic acidBiochemistryMedicinal chemistryAdductchemistry.chemical_compoundchemistryDrug DiscoveryMichael reactionOrganic chemistryMoietyEnantiomerOxidative decarboxylationCarbaniondescription
The reaction of the lithium enolate of the 1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with α,β-unsaturated carbonyl compounds proceeds readily to give the corresponding Michael adducts in good yields and high diastereoselectivity. Subsequent basic hydrolysis of the acetal and oxidative decarboxylation of the α-hydroxyacid moiety provides chiral 2-substituted 1,4-dicarbonyl compounds with very high enantiomeric excesses.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-11-01 | ChemInform |