2024
Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis
Guo M, Miller S. Catalyst–Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis. ACS Catalysis 2024, 17226-17232. DOI: 10.1021/acscatal.4c05014.Peer-Reviewed Original ResearchChiral phosphoric acidPositive nonlinear effectNon-covalent interactionsQuinazolinone synthesisHeterocyclic systemsCatalyst scaffoldHigh enantioselectivityNitrogen heteroatomsEnantiomeric ratioCatalystReaction developmentCatalytic scaffoldMechanistic studiesEnantioselectivityPhosphoric acidSubstrateCarbocyclesCyclocondensationHeterocyclesHeteroatomsScaffoldsReactionSynthesisReactivityYield
2017
A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides
Cussó O, Giuliano MW, Ribas X, Miller SJ, Costas M. A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides. Chemical Science 2017, 8: 3660-3667. PMID: 29270284, PMCID: PMC5734052, DOI: 10.1039/c7sc00099e.Peer-Reviewed Original ResearchIron centerHigh enantioselectivityIron coordination complexesAqueous hydrogen peroxideSecond coordination sphereΒ-turn structureShort reaction timesTerminal carboxylic acidSupramolecular catalystsCoordination complexesSupramolecular systemsClasses of substratesAsymmetric catalysisCoordination sphereAsymmetric epoxidationExcellent yieldsCarboxylic acidsCombination of peptidesActivation stepHydrogen peroxideReaction timeEpoxidationEnantioselectivityPeptidesCatalyst
2015
Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination
Diener ME, Metrano AJ, Kusano S, Miller SJ. Enantioselective Synthesis of 3‑Arylquinazolin-4(3H)‑ones via Peptide-Catalyzed Atroposelective Bromination. Journal Of The American Chemical Society 2015, 137: 12369-12377. PMID: 26343278, PMCID: PMC5134330, DOI: 10.1021/jacs.5b07726.Peer-Reviewed Original ResearchConceptsAtroposelective brominationDensity functional theory calculationsBroad substrate scopeX-ray crystallographyΒ-turn peptideFunctional theory calculationsCross-coupling sequenceFree catalystsSubstrate scopeAmination procedureStereochemical informationEnantioselective synthesisTheory calculationsHigh enantioselectivityRotational barriersMechanistic studiesSubsequent transformationBrominationMono-orthoProduct of interestCatalystEnantioinductionCrystallographyEnantioselectivityIsomers