Publication | Closed Access
Assembly of Enantioenriched <i>cis</i>‐3a,8a‐Hexahydropyrrolo[2,3‐<i>b</i>]indole Scaffolds by Silver(I)‐Catalyzed Asymmetric Domino Reaction of Isocyanoacetates in the Presence of <i>Cinchona</i>‐Derived Chiral Phosphorus Ligands
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Citations
48
References
2016
Year
Asymmetric CatalysisBioorganic ChemistryAsymmetric Domino ReactionEngineeringNatural SciencesDiversity-oriented SynthesisChiral Phosphorus LigandsOrganic ChemistryCatalytic LigandsCatalysisStereoselective SynthesisChemistryNatural Product SynthesisChiral PhosphinesSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringAvailable Isocyanoacetates
Abstract By using Cinchona ‐derived chiral phosphines as catalytic ligands, enantioenriched cis ‐3a,8a‐hexahydropyrrolo[2,3‐ b ]indoles ( ent ‐HPIs), which are core scaffolds in a large array of biologically active natural products, can be convergently assembled under mild conditions through the silver(I)‐catalyzed asymmetric domino reaction of readily available isocyanoacetates and 2‐(2‐aminophenyl)acrylates. Various functionalities can be tolerated in the reaction, affording enantioenriched HPIs in high overall yields and good enantioselectivities (up to 92% ee s). magnified image
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