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RESEARCH PRODUCT
Asymmetric Synthesis of Functionalized Tricyclic Chromanes via an Organocatalytic Triple Domino Reaction
Arto ValkonenMukesh KumarKari RissanenPankaj ChauhanDieter Enderssubject
chemistry.chemical_classification010405 organic chemistryasymmetric synthesisOrganic ChemistryEnantioselective synthesistricyclic chromanes010402 general chemistry01 natural sciencesBiochemistryDomino0104 chemical sciencesStereocenterchemistry.chemical_compoundCascade reactionchemistrytriple domino reactionChromaneOrganic chemistryAldol condensationStereoselectivityPhysical and Theoretical Chemistryta116Tricyclicdescription
A highly stereoselective triple domino reaction for the synthesis of functionalized tricyclic chromane scaffolds has been developed. A secondary amine-catalyzed domino Michael/Michael/aldol condensation reaction between aliphatic aldehydes, nitro-chromenes, and α,β-unsaturated aldehydes leads to the formation of synthetically important tricyclic chromanes bearing four contiguous stereogenic centers including a tetrasubstituted carbon in good yields (20–66%) and excellent stereoselectivities (>20:1 dr and >99% ee).
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-05-23 | Organic Letters |