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
2018
Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration
Kwon Y, Chinn AJ, Kim B, Miller SJ. Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C−N Bond‐Forming Cross‐Coupling and Catalyst‐Controlled Atroposelective Cyclodehydration. Angewandte Chemie International Edition 2018, 57: 6251-6255. PMID: 29637680, PMCID: PMC5964046, DOI: 10.1002/anie.201802963.Peer-Reviewed Original ResearchConceptsAxis of chiralityCopper complexesChiral phosphoric acid catalystChiral copper complexesPhosphoric acid catalystStereogenic carbon centersMultiple stereoisomersCatalytic approachCatalytic reactionStereogenic elementsAcid catalystRemote desymmetrizationCatalyst controlAxial chiralityCarbon centerStereogenic centersCross couplingHigh diastereoselectivityPhosphoric acidCatalystChiralityStereoisomersCyclodehydrationStereogenicityReaction