2022
Imine Directed Cp*RhIII‐Catalyzed N−H Functionalization and Annulation with Amino Amides, Aldehydes, and Diazo Compounds
Zoll A, Molas J, Mercado B, Ellman J. Imine Directed Cp*RhIII‐Catalyzed N−H Functionalization and Annulation with Amino Amides, Aldehydes, and Diazo Compounds. Angewandte Chemie 2022, 135 DOI: 10.1002/ange.202210822.Peer-Reviewed Original ResearchDiazo compoundsAmino amidesX-ray crystallographic characterizationFive-membered rhodacycleAmino acid side chainsAcid side chainsRange of functionalitiesCrystallographic characterizationAlkyl aldehydesSide chainsEfficient reactantsFunctionalizationMinimal racemizationFirst exampleMechanistic studiesIminesAldehydesAnnulationAmidesEfficient transformationCompoundsCatalyzedPiperazinonesRhodacycleReactantsImine Directed Cp*RhIII‐Catalyzed N−H Functionalization and Annulation with Amino Amides, Aldehydes, and Diazo Compounds
Zoll A, Molas J, Mercado B, Ellman J. Imine Directed Cp*RhIII‐Catalyzed N−H Functionalization and Annulation with Amino Amides, Aldehydes, and Diazo Compounds. Angewandte Chemie International Edition 2022, 62: e202210822. PMID: 36331194, PMCID: PMC9805510, DOI: 10.1002/anie.202210822.Peer-Reviewed Original ResearchConceptsDiazo compoundsH functionalizationAmino amidesX-ray crystallographic characterizationFive-membered rhodacycleAmino acid side chainsAcid side chainsRange of functionalitiesCrystallographic characterizationAlkyl aldehydesSide chainsEfficient reactantsFunctionalizationMinimal racemizationFirst exampleMechanistic studiesIminesAldehydesAnnulationEfficient transformationAmidesCompoundsCatalyzedPiperazinonesRhodacycle
2018
RhIII‐Catalyzed Synthesis of Isoquinolones and 2‐Pyridones by Annulation of N‐Methoxyamides and Nitroalkenes
Potter TJ, Li Y, Ward MD, Ellman JA. RhIII‐Catalyzed Synthesis of Isoquinolones and 2‐Pyridones by Annulation of N‐Methoxyamides and Nitroalkenes. European Journal Of Organic Chemistry 2018, 2018: 4381-4388. PMID: 30220876, PMCID: PMC6136657, DOI: 10.1002/ejoc.201800745.Peer-Reviewed Original ResearchSingle-crystal X-ray diffractionCrystal X-ray diffractionX-ray diffractionInclusion complexesH bondsHost frameworkN-methoxyamidesRelative stereochemistryNitroalkenesAnnulationAromatic nitroalkenesIsoquinolonesRoom temperatureSynthesisAlkenylStereochemistryMethoxyamidesBondsAromaticsDiffractionCompoundsComplexesAcidMaterialsOilRhodium(III)-Catalyzed Imidoyl C–H Activation for Annulations to Azolopyrimidines
Halskov KS, Witten MR, Hoang GL, Mercado BQ, Ellman JA. Rhodium(III)-Catalyzed Imidoyl C–H Activation for Annulations to Azolopyrimidines. Organic Letters 2018, 20: 2464-2467. PMID: 29582661, PMCID: PMC5941131, DOI: 10.1021/acs.orglett.8b00816.Peer-Reviewed Original Research
2014
A Lewis Acid Catalyzed Annulation to 2,1-Benzisoxazoles
Otley KD, Ellman JA. A Lewis Acid Catalyzed Annulation to 2,1-Benzisoxazoles. The Journal Of Organic Chemistry 2014, 79: 8296-8303. PMID: 25157596, PMCID: PMC4156248, DOI: 10.1021/jo5015432.Peer-Reviewed Original ResearchConceptsInitial mechanistic investigationsLewis Acid‐Catalyzed AnnulationFriedel-Crafts cyclizationConvergent routeSubstrate scopeReaction intermediatesCompound classesGlyoxylate estersCatalyzed AnnulationO-selectivityUmpolung additionMechanistic investigationsConvenient conditionsHigh yieldsAnnulationBenzisoxazoleDeveloped methodNitrosoarenesNitrosobenzeneCyclizationNew typeIntermediatesSynthesisReactionEsters
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