Publication | Closed Access
Enantioselective Syntheses of Tetrahydroquinolines Based on Iridium‐Catalyzed Allylic Substitutions: Total Syntheses of (+)‐Angustureine and (–)‐Cuspareine
38
Citations
61
References
2011
Year
EngineeringOne‐pot HydroborationProtecting‐group‐free Two‐step ApproachNatural SciencesDiversity-oriented SynthesisAllylic AminationEnantioselective SynthesesOrganic ChemistryCatalysisIridium‐catalyzed Allylic SubstitutionsChemistryTotal SynthesesPharmacologyAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
Abstract A protecting‐group‐free two‐step approach for the preparation of tetrahydroquinolines has been developed. The procedure involves a highly regio‐ and enantioselective intermolecular iridium‐catalyzed allylic amination followed by one‐pot hydroboration and intramolecular Suzuki–Miyaura cross‐coupling. This method was applied in total syntheses of the alkaloids (+)‐angustureine and (–)‐cuspareine.
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