0000000001309550

AUTHOR

Uğur Kaya

showing 15 related works from this author

Diastereoselective Synthesis of Spiro[pyrazolone-4,3′-tetrahydrothiophenes] via a Sulfa-Michael/Aldol Domino Reaction

2016

Synthesis : journal of synthetic organic chemistry 48(23), 4091-4098(2016). doi:10.1055/s-0035-1562473

Reaction conditions010405 organic chemistryChemistryOrganic ChemistryPyrazolone010402 general chemistry54001 natural sciencesCombinatorial chemistryCatalysisDomino0104 chemical scienceschemistry.chemical_compoundCascade reactionAldol reactionYield (chemistry)ddc:540medicineOrganic chemistryTetrahydrothiophenemedicine.drug
researchProduct

Asymmetric Synthesis of Spiro β-Lactamsviaa Squaramide- Catalyzed Sulfa-Michael Addition/Desymmetrization Protocol

2016

An efficient asymmetric synthesis of spirocyclohexenone β-lactams bearing three contiguous stereocenters has been achieved in moderate to good yields and high stereoselectivities. The protocol involves the combination of a squaramide-catalyzed sulfa-Michael addition under desymmetrization via a dynamic kinetic resolution of racemic 2,5-cyclohexadienones.

010405 organic chemistryChemistryStereochemistrybeta-lactamsasymmetric synthesisEnantioselective synthesisSquaramideGeneral Chemistry010402 general chemistry01 natural sciencesDesymmetrization0104 chemical sciencesKinetic resolutionStereocenterCatalysisOrganocatalysisMichael reactionta116Advanced Synthesis & Catalysis
researchProduct

Enantioselective synthesis of pyrazolone α-aminonitrile derivatives via an organocatalytic Strecker reaction

2017

A new organocatalytic enantioselective Strecker reaction of pyrazolone-derived ketimine electrophiles has been developed. Using pseudo-enantiomeric squaramide catalysts the nucleophilic 1,2-addition of trimethylsilyl cyanide to the ketimines efficiently provides a direct entry to both enantiomers of pyrazolone α- aminonitrile derivatives at will in good yields and high enantioselectivities for a wide variety of substrates. peerReviewed

Strecker amino acid synthesisPyrazolone010402 general chemistry01 natural sciencesCatalysischemistry.chemical_compoundNucleophileMaterials ChemistrymedicineOrganic chemistryenantioselective synthesisTrimethylsilyl cyanideta116010405 organic chemistryMetals and AlloysSquaramideEnantioselective synthesisGeneral Chemistry0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialschemistryStrecker reactionElectrophileCeramics and CompositesEnantiomermedicine.drug
researchProduct

Squaramide-Catalyzed Asymmetric aza-Friedel-Crafts/N,O-Acetalization Domino Reactions Between 2-Naphthols and Pyrazolinone Ketimines

2017

N-Boc ketimines derived from pyrazolin-5-ones were explored to develop an unprecedented domino aza-Friedel-Crafts/N,O-acetalization reaction with 2-naphthols. The novel method requires a catalyst loading of only 0.5 mol % of a bifunctional squaramide catalyst, is scalable to gram amounts, and provides a new series of furanonaphthopyrazolidinone derivatives bearing two vicinal tetra-substituted stereogenic centers in excellent yields (95-98 %) and stereoselectivity (>99:1 d.r. and 97-98 % ee). A different reactivity was observed in the case of 1-naphthols and other electron-rich phenols, which led to the aza-Friedel-Crafts adducts in 70-98 % yield and 47-98 % ee.

010405 organic chemistryChemistrydomino reactionsEnantioselective synthesisSquaramideGeneral MedicineGeneral Chemistry010402 general chemistry01 natural sciencesMedicinal chemistryCatalysisDomino0104 chemical sciencesStereocenterCatalysischemistry.chemical_compoundOrganocatalysisYield (chemistry)StereoselectivityReactivity (chemistry)Bifunctionalta116Friedel–Crafts reactionAngewandte Chemie International Edition
researchProduct

Asymmetric Synthesis of Tetrahydrobenzofurans and Annulated Dihydropyrans via Cooperative One-Pot Organo- and Silver-Catalysis

2016

Synthesis : journal of synthetic organic chemistry 48(19), 3207-3216(2016). doi:10.1055/s-0035-1561468

Annulation010405 organic chemistryChemistryOrganic ChemistryOne-pot synthesisEnantioselective synthesisSquaramide540010402 general chemistry01 natural sciencesCombinatorial chemistryCatalysis0104 chemical sciencesCatalysisOrganocatalysisddc:540Michael reactionOrganic chemistryHydroalkoxylationSynthesis
researchProduct

Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

2015

Chemical communications 52(8), 1669-1672(2016). doi:10.1039/C5CC09592A

010402 general chemistry01 natural sciencescatalystsCatalysisCatalysisMichael additionMaterials ChemistryOrganic chemistryenantioselective synthesista116Hydroalkoxylation010405 organic chemistryChemistryMetals and AlloysSquaramideEnantioselective synthesisGeneral Chemistry540hydroalkoxylation0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic Materialspyranonaphthoquinonesddc:540Ceramics and CompositesMichael reactionChemical Communications
researchProduct

Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction.

2017

A new series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in asymmetric Mannich reactions with pyrazolones. The amino-bis-pyrazolone products are obtained in excellent yields and stereoselectivities by employing a very low loading of 1 mol % of a bifunctional squaramide organocatalyst. Depending on the substitution at position 4 of the pyrazolones, the new protocol allows for the generation of one or two tetrasubstituted stereocenters, including a one-pot version combing the Mannich reaction with a base-mediated halogenation. peerReviewed

Mannich reactions010405 organic chemistryChemistryOrganic Chemistryasymmetric synthesisSquaramideEnantioselective synthesisHalogenation010402 general chemistry01 natural sciencespyrazolones0104 chemical sciencesStereocenteramino-bis-pyrazolone productschemistry.chemical_compoundElectrophilePyrazolonesOrganic chemistryBifunctionalMannich reactionta116The Journal of organic chemistry
researchProduct

CCDC 1542055: Experimental Crystal Structure Determination

2017

Related Article: Suruchi Mahajan, Pankaj Chauhan, Uğur Kaya, Kristina Deckers, Kari Rissanen, Dieter Enders|2017|Chem.Commun.|53|6633|doi:10.1039/C7CC02874A

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1-(4-chlorophenyl)-3-methyl-5-oxo-4-(phenylamino)-45-dihydro-1H-pyrazole-4-carbonitrileExperimental 3D Coordinates
researchProduct

CCDC 1474771: Experimental Crystal Structure Determination

2016

Related Article: Uğur Kaya, Pankaj Chauhan, Kristina Deckers, Rakesh Puttreddy, Kari Rissanen, Gerhard Raabe, Dieter Enders|2016|Synthesis|48|3207|doi:10.1055/s-0035-1561468

2-benzylidene-3-(nitromethyl)-3567-tetrahydro-1-benzofuran-4(2H)-oneSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1474975: Experimental Crystal Structure Determination

2016

Related Article: Uğur Kaya, Pankaj Chauhan, Kristina Deckers, Rakesh Puttreddy, Kari Rissanen, Gerhard Raabe, Dieter Enders|2016|Synthesis|48|3207|doi:10.1055/s-0035-1561468

Space GroupCrystallography13-dimethyl-5-(nitromethyl)-7-phenyl-15-dihydro-2H-pyrano[23-d]pyrimidine-24(3H)-dioneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1537523: Experimental Crystal Structure Determination

2017

Related Article: Pankaj Chauhan, Suruchi Mahajan, Uğur Kaya, Anssi Peuronen, Kari Rissanen, and Dieter Enders|2017|J.Org.Chem.|82|7050|doi:10.1021/acs.joc.7b01113

Space GroupCrystallographyCrystal SystemCrystal Structuret-butyl [3'4-dimethyl-55'-dioxo-11'-diphenyl-3-(phenylethynyl)[1'455'-tetrahydro-1H4'H-[44'-bipyrazole]]-4'-yl]carbamateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1537522: Experimental Crystal Structure Determination

2017

Related Article: Pankaj Chauhan, Suruchi Mahajan, Uğur Kaya, Anssi Peuronen, Kari Rissanen, and Dieter Enders|2017|J.Org.Chem.|82|7050|doi:10.1021/acs.joc.7b01113

4'-[(t-butoxycarbonyl)amino]-33'-dimethyl-5'-oxo-11'-diphenyl[4'5'-dihydro-1H1'H-[44'-bipyrazole]]-5-yl acetateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1476009: Experimental Crystal Structure Determination

2016

Related Article: Pankaj Chauhan, Suruchi Mahajan, Uğur Kaya, Arto Valkonen, Kari Rissanen and Dieter Enders|2016|Adv.Synth.Catal.|358|3173|doi:10.1002/adsc.201600554

Space GroupCrystallographyethyl 1-benzyl-9-((2-bromophenyl)sulfanyl)-27-dioxo-1-azaspiro[3.5]non-5-ene-3-carboxylateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1437688: Experimental Crystal Structure Determination

2015

Related Article: Uğur Kaya, Pankaj Chauhan, Daniel Hack, Kristina Deckers, Rakesh Puttreddy, Kari Rissanen, Dieter Enders|2016|Chem.Commun.|52|1669|doi:10.1039/C5CC09592A

Space GroupCrystallographyCrystal SystemCrystal Structure(R)-2-(2-Bromophenyl)-4-(nitromethyl)-4H-benzo[g]chromene-510-dioneCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1572983: Experimental Crystal Structure Determination

2017

Related Article: Uğur Kaya, Pankaj Chauhan, Suruchi Mahajan, Kristina Deckers, Arto Valkonen, Kari Rissanen, Dieter Enders|2017|Angew.Chem.,Int.Ed.|56|15358|doi:10.1002/anie.201709224

Space GroupCrystallographyCrystal SystemCrystal Structuret-butyl (7a-methyl-10-oxo-9-phenyl-7a8910-tetrahydro-10aH-naphtho[1'2':45]furo[23-c]pyrazol-10a-yl)carbamateCell ParametersExperimental 3D Coordinates
researchProduct