2024
Fe/Thiol Cooperative Hydrogen Atom Transfer Olefin Hydrogenation: Mechanistic Insights That Inform Enantioselective Catalysis
Buzsaki S, Mason S, Kattamuri P, Serviano J, Rodriguez D, Wilson C, Hood D, Ellefsen J, Lu Y, Kan J, West J, Miller S, Holland P. Fe/Thiol Cooperative Hydrogen Atom Transfer Olefin Hydrogenation: Mechanistic Insights That Inform Enantioselective Catalysis. Journal Of The American Chemical Society 2024, 146: 17296-17310. PMID: 38875703, PMCID: PMC11209773, DOI: 10.1021/jacs.4c04047.Peer-Reviewed Original ResearchMetal-catalyzed hydrogen atom transferChiral thiolsAsymmetric hydrogenationSynthesis of complex moleculesMinimally functionalized olefinsSelectivity-determining stepTransition metal catalysisHydrogen atom transferOff-cycle speciesH-atom donorsTransfer of hydrideAsymmetric inductionElectron-richAtom transferMetal catalysisEnantioselective reductionThiol catalystMetal catalystsAlkyl radicalsElectron-neutralIron speciesOlefinsTraditional hydrogenationEnantiomeric ratioRadical catalysis
2013
The 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