6533b829fe1ef96bd128afc8
RESEARCH PRODUCT
Diastereoselective Michael Addition of (S)-Mandelic Acid Enolate to Nitroalkenes. Enantioselective Synthesis of α-Hydroxy-α,β-diaryl-γ-lactams.
Isabel FernándezGonzalo BlayBelen MonjeJosé R. Pedrosubject
StereochemistryOrganic ChemistryAcetalEnantioselective synthesisGeneral MedicineMandelic acidBiochemistryMedicinal chemistryAdductchemistry.chemical_compoundAminolysischemistryDrug DiscoveryMichael reactionNitroMoietydescription
Abstract The reaction of the lithium enolate of the ( S , S )- cis -1,3-dioxolan-4-one derived from optically active ( S )-mandelic acid and pivalaldehyde with several aromatic nitroalkenes in the presence of HMPA proceeds readily to give the corresponding Michael adducts in good yields and diastereoselectivities. Reduction of the nitro group with Zn/HCl/EtOH/H 2 O with concomitant intramolecular aminolysis of the acetal moiety leads directly to enantiomerically pure α-hydroxy-α,β-diaryl-γ-lactams.
year | journal | country | edition | language |
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2004-05-18 | ChemInform |