0000000000726928

AUTHOR

Marcus Blümel

showing 8 related works from this author

Asymmetric Synthesis of Spiro Tetrahydrothiophene-indan-1,3-diones via a Squaramide-Catalyzed Sulfa-Michael/Aldol Domino Reaction

2016

Synthesis 48(08), 1131-1138(2016). doi:10.1055/s-0035-1560412

chemistry.chemical_classificationSpiro compound010405 organic chemistryOrganic ChemistrySquaramideEnantioselective synthesis540010402 general chemistry01 natural sciencesMedicinal chemistryCatalysisDomino0104 chemical scienceschemistry.chemical_compoundchemistryCascade reactionAldol reactionOrganocatalysisddc:540Organic chemistryTetrahydrothiophene
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Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro-1,2-Diazepinones by NHC-Catalyzed [3+4] Annulation Reactions

2016

A strategy for the NHC-catalyzed asymmetric synthesis of spirobenzazepinones, spiro-1,2-diazepinones, and spiro-1,2-oxazepinones has been developed via [3+4]-cycloaddition reactions of isatin-derived enals (3C component) with in-situ-generated aza-o-quinone methides, azoalkenes, and nitrosoalkenes (4atom components). The [3+4] annulation strategy leads to the seven-membered target spiro heterocycles bearing an oxindole moiety in high yields and excellent enantioselectivities with a wide variety of substrates. Notably, the benzazepinone synthesis is atroposelective and an all-carbon spiro stereocenter is generated.

chemistry.chemical_classificationAnnulationSpiro compound010405 organic chemistryStereochemistry2-diazepinone1asymmetric synthesisEnantioselective synthesisGeneral MedicineGeneral Chemistrybenzazepinonespiro compound010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesStereocenterCatalysischemistry.chemical_compoundchemistryMoietyOxindoleta116N-heterocyclic carbeneAngewandte Chemie International Edition
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Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketim…

2017

A novel NHC-catalyzed annulation protocol for the asymmetric synthesis of biologically important β-lactam fused spirocyclopentane oxindoles with four contiguous stereocenters, including two quaternary carbon centers, was developed. Alternatively, spirocyclopentane oxindoles containing an enaminone moiety can be achieved using the same starting materials, isatin-derived enals, and N-sulfonyl ketimines, in the presence of a slightly different NHC catalytic system. This switchable annulation strategy enables the selective assembly of both heterocyclic scaffolds with good yields and excellent enantioselectivities for a broad range of substrates.

Annulationasymmetric synthesis010402 general chemistry01 natural sciencesCatalysisStereocenterchemistry.chemical_compoundkatalyytitMoietyOrganic chemistryorganocatalysisN-heterocyclic carbenesheterosykliset yhdisteetspiro-compoundsta116Sulfonylchemistry.chemical_classificationkemiallinen synteesiheterocycles010405 organic chemistryIsatinEnantioselective synthesisGeneral ChemistryGeneral Medicine0104 chemical scienceschemistryOrganocatalysisCarbeneAngewandte Chemie
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CCDC 1534938: Experimental Crystal Structure Determination

2017

Related Article: Lei Wang, Sun Li, Marcus Blümel, Rakesh Puttreddy, Anssi Peuronen, Kari Rissanen, Dieter Enders|2017|Angew.Chem.,Int.Ed.|56|8516|doi:10.1002/anie.201704210

Space GroupCrystallography1'-benzyl-5'-fluoro-6-[(4-methylphenyl)sulfonyl]-35-diphenyl-7H-spiro[6-azabicyclo[3.2.0]heptane-23'-indole]-2'7(1'H)-dioneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1453056: Experimental Crystal Structure Determination

2016

Related Article: Lei Wang, Sun Li, Marcus Blümel, Arne R. Philipps, Ai Wang, Rakesh Puttreddy, Kari Rissanen, Dieter Enders|2016|Angew.Chem.,Int.Ed.|55|11110|doi:10.1002/anie.201604819

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters9-methyl-1-((4-methylphenyl)sulfonyl)-1'-phenyl-15-dihydrospiro[1-benzazepine-43'-indole]-22'(1'H3H)-dione ethanol solvateExperimental 3D Coordinates
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CCDC 1413502: Experimental Crystal Structure Determination

2016

Related Article: Lei Wang, Sun Li, Marcus Blümel, Arne R. Philipps, Ai Wang, Rakesh Puttreddy, Kari Rissanen, Dieter Enders|2016|Angew.Chem.,Int.Ed.|55|11110|doi:10.1002/anie.201604819

Space GroupCrystallographyCrystal SystemCrystal Structure1'-benzyl-2-((4-methylphenyl)sulfonyl)-5a6-dihydro-2H-spiro[chromeno[43-c][12]diazepine-53'-indole]-2'3(1'H4H)-dioneCell ParametersExperimental 3D Coordinates
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CCDC 1437740: Experimental Crystal Structure Determination

2016

Related Article: Suruchi Mahajan, Pankaj Chauhan, Marcus Blümel, Rakesh Puttreddy, Kari Rissanen, Gerhard Raabe, Dieter Enders|2016|Synthesis|48|1131|doi:10.1055/s-0035-1560412

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters13-Dioxo-2'-phenyl-134'5'-tetrahydrospiro[indene-23'-thiophen]-4'-yl phenylcarbamateExperimental 3D Coordinates
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CCDC 1527542: Experimental Crystal Structure Determination

2017

Related Article: Lei Wang, Sun Li, Marcus Blümel, Rakesh Puttreddy, Anssi Peuronen, Kari Rissanen, Dieter Enders|2017|Angew.Chem.,Int.Ed.|56|8516|doi:10.1002/anie.201704210

Space GroupCrystallographyCrystal SystemCrystal StructureN-{[1'-benzyl-2-(4-chlorophenyl)-2'4-dioxo-1'2'-dihydro-3H-spiro[cyclopentane-13'-indol]-3-ylidene](phenyl)methyl}-4-methylbenzene-1-sulfonamide ethyl acetate solvateCell ParametersExperimental 3D Coordinates
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