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RESEARCH PRODUCT
Organocatalytic Oxa-Michael/Michael/Michael/Aldol Condensation Quadruple Domino Sequence : Asymmetric Synthesis of Tricyclic Chromanes
Stephen J. BaileyCarolina Von EssenDieter EndersKari RissanenMukesh KumarEhsan JafariPankaj Chauhansubject
synthesisalkoholit (yhdisteet)natural productsStereochemistryasymmetric synthesisluonnontuotteet010402 general chemistry01 natural sciencesBiochemistryDominoStereocenterchemistry.chemical_compoundCascade reactionsynteesiPhysical and Theoretical Chemistryta116chemistry.chemical_classification010405 organic chemistryOrganic ChemistryAcroleindomino reactionsEnantioselective synthesistricyclic chromanes0104 chemical scienceschemistryalcohols (organic compounds)asymmetriaAldol condensationStereoselectivityasymmetryTricyclicdescription
An efficient and highly stereoselective one-pot, four-component synthesis of functionalized tricyclic chromanes has been achieved through an organocatalyzed quadruple domino reaction. The reaction sequence involves an oxa-Michael/Michael/Michael/aldol condensation between alcohols, 2 equiv of acrolein, and nitrochromenes to generate the pharmaceutically important tricyclic chromanes bearing three contiguous stereogenic centers including a chiral tetrasubstituted carbon center in good domino yields (30–70%) and excellent diastereo- and enantioselectivities (>20:1 dr and >99% ee). peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-01-01 |