0000000000087655

AUTHOR

Tõnis Kanger

showing 6 related works from this author

CaCl2, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

2015

A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.

Bisoxazolineinorganic chemicalsAminoindanol010405 organic chemistryChemistryLigandOrganic ChemistryMalonateCaCl2macromolecular substances010402 general chemistrybehavioral disciplines and activities01 natural sciencesDimethyl malonatehumanities0104 chemical sciencesCatalysisAdductchemistry.chemical_compoundMalonateMichael reactionOrganic chemistryLewis acids and basesta116The Journal of Organic Chemistry
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Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution

2017

A general platform for the synthesis of various chiral halogen-bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X-ray crystallography and in solution by 1H NMR titration can be used to aid the design of new XB donors. We describe the first example of a XB between iodotriazoles and thioureas in solution. In addition, the enantiodiscrimination of acceptors in solution through halogen-bond participation is described.

TriazoleSolid-state010402 general chemistry01 natural scienceschemical bondsCatalysiskemialliset sidoksetchemistry.chemical_compoundNMR spectroscopyhalogensOrganic chemistryNMR-spektroskopiata116x-ray crystallographykemiallinen synteesiHalogen bondhalogeenit010405 organic chemistryOrganic ChemistryGeneral ChemistryCombinatorial chemistry0104 chemical scienceschemistryHalogenTitrationröntgenkristallografiachemical synthesisChemistry - A European Journal
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Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles

2016

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles in high enantiomeric purities.

asymmetric organocatalytic wittigIndolesStereoisomerism010402 general chemistry01 natural sciencesBiochemistryCatalysisCatalysischemistry.chemical_compoundCombinatorial Chemistry TechniquesOrganic chemistryOxindolePhysical and Theoretical Chemistryta116Molecular Structure010405 organic chemistryOrganic ChemistrySquaramideEnantioselective synthesisStereoisomerismAmidesOxindoles0104 chemical scienceschemistryWittig reactionEnantiomerOrganic Letters
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CCDC 1056977: Experimental Crystal Structure Determination

2015

Related Article: Kristin Lippur , Sandra Kaabel , Ivar Järving , Kari Rissanen , and Tõnis Kanger|2015|J.Org.Chem.|80|6336|doi:10.1021/acs.joc.5b00769

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D CoordinatesDimethyl (S)-2-(1-(4-nitrophenyl)-14-dioxopentan-3-yl)malonate
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CCDC 1447017: Experimental Crystal Structure Determination

2016

Related Article: Maksim Ošeka, Mariliis Kimm, Sandra Kaabel, Ivar Järving, Kari Rissanen, and Tõnis Kanger|2016|Org.Lett.|18|1358|doi:10.1021/acs.orglett.6b00291

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates3-(1-(4-chlorophenyl)prop-2-en-1-yl)-3-hydroxy-1-(4-methylbenzyl)-13-dihydro-2H-indol-2-one
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CCDC 1447018: Experimental Crystal Structure Determination

2016

Related Article: Maksim Ošeka, Mariliis Kimm, Sandra Kaabel, Ivar Järving, Kari Rissanen, and Tõnis Kanger|2016|Org.Lett.|18|1358|doi:10.1021/acs.orglett.6b00291

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters7-fluoro-3-hydroxy-1-(4-methylbenzyl)-3-(1-phenylprop-2-en-1-yl)-13-dihydro-2H-indol-2-oneExperimental 3D Coordinates
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