2017
Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst
Chinn AJ, Kim B, Kwon Y, Miller SJ. Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst. Journal Of The American Chemical Society 2017, 139: 18107-18114. PMID: 29116792, PMCID: PMC5738244, DOI: 10.1021/jacs.7b11197.Peer-Reviewed Original ResearchConceptsComplex molecular settingsO bond formationPeptide-based ligandsCross-coupling reactionsPhenolic hydroxyl groupsIntermolecular CuIntermolecular CChemoselective reactionTBu groupBond formationAppreciable selectivityReactive sitesPhenolic nucleophilesHydroxyl groupsSteric perturbationsMaximum enantioselectivitySecond reactive siteMolecular settingNucleophilesDesymmetrizationUncommon levelReactionSubstrateCatalystChemistry
2013
A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation
Chandler BD, Burkhardt AL, Foley K, Cullis C, Driscoll D, D’Amore N, Miller SJ. A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation. Journal Of The American Chemical Society 2013, 136: 412-418. PMID: 24344932, PMCID: PMC3919123, DOI: 10.1021/ja410750a.Peer-Reviewed Original ResearchThe Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry
Osuna S, Dermenci A, Miller SJ, Houk KN. The Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry. Chemistry - A European Journal 2013, 19: 14245-14253. PMID: 24038400, PMCID: PMC3918516, DOI: 10.1002/chem.201300745.Peer-Reviewed Original ResearchConceptsRauhut-Currier reactionCysteine derivativesComplete reaction pathwayRole of counterionsPresence of counterionsRate-determining eliminationMichael addition productsDensity functional theoryComputational chemistryExplicit water solvationWater solvationPotassium counterionsReaction conditionsReaction pathwaysAddition productsEnantiomer pairsThiol catalystCatalyst eliminationPossible stereoisomersCurrier ReactionFunctional theoryCounterionsNucleophilesReactionDerivatives
2011
Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities
Dermenci A, Selig PS, Domaoal RA, Spasov KA, Anderson KS, Miller SJ. Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities. Chemical Science 2011, 2: 1568-1572. PMID: 24179673, PMCID: PMC3811095, DOI: 10.1039/c1sc00221j.Peer-Reviewed Original Research