0000000000011894

AUTHOR

Tao Shu

showing 10 related works from this author

Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

2016

An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes is described.

CyclopentanesStereochemistry010402 general chemistry01 natural sciencesCatalysisDominoCatalysisStereocenterCascade reactiondomino reactionMaterials Chemistryta116cyclopentane motifs010405 organic chemistryChemistryMetals and AlloysEnantioselective synthesisGeneral Chemistry5400104 chemical sciences3. Good healthSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsChemistryddc:540Ceramics and CompositesChemical communications (Cambridge, England)
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ChemInform Abstract: Asymmetric Synthesis of Cyclopentanes Bearing Four Contiguous Stereocenters via an NHC-Catalyzed Michael/Michael/Esterification …

2016

An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.

CyclopentanesBearing (mechanical)Cascade reactionlawChemistryStereochemistryEnantioselective synthesisGeneral MedicineDominolaw.inventionCatalysisStereocenterChemInform
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Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

2018

The first example of an N-heterocyclic carbene-catalyzed asymmetric desymmetrization of enal-tethered cyclohexadienones via an intramolecular homoenolate Michael addition/esterification reaction is described. This new protocol offers a direct entry to various functionalized tetrahydrofluorenones with three contiguous stereocenters in high yields, good diastereoselectivities and excellent enantioselectivities.

aromaattiset yhdisteet010402 general chemistry01 natural sciencesDesymmetrizationCatalysisStereocenterCatalysisDirect entryMaterials Chemistryta116kemiallinen synteesi010405 organic chemistryChemistryaromatic compoundsMetals and AlloysEnantioselective synthesisGeneral ChemistryCombinatorial chemistry0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsIntramolecular forceCeramics and CompositesMichael reactionEsterification reactionchemical synthesisChemical Communications
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Asymmetric Synthesis of Spirocyclic β-Lactams through Copper-Catalyzed Kinugasa/Michael Domino Reactions

2018

The first copper-catalyzed highly chemo-, regio-, diastereo-, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne-tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β-lactams possessing four contiguous stereocenters, including one quaternary and one tetra-substituted stereocenter.

Molecular Structure010405 organic chemistryStereochemistryChemistryasymmetric synthesisEnantioselective synthesisGeneral MedicineGeneral Chemistrybeta-Lactams010402 general chemistry01 natural sciencesDesymmetrizationCatalysisDomino0104 chemical sciencesCatalysisStereocenterCascade reactionAlkynesβ lactamsStereoselectivityta116CopperAngewandte Chemie International Edition
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Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions

2018

The first copper‐catalyzed highly chemo‐, regio‐, diastereo‐, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne‐tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β‐lactams possessing four contiguous stereocenters, including one quaternary and one tetra‐substituted stereocenter. peerReviewed

asymmetric synthesis
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Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.

2016

An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).

chromansAddition reaction010405 organic chemistrydomino reactionspara-quinone methidesEnantioselective synthesisGeneral MedicineGeneral Chemistry010402 general chemistry01 natural sciencesoxa-Michael additionCatalysisDomino0104 chemical sciencesStereocenterchemistry.chemical_compoundchemistryCascade reactionOrganocatalysisOrganic chemistryorganocatalysisOxindoleBifunctionalta116Angewandte Chemie (International ed. in English)
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CCDC 1831622: Experimental Crystal Structure Determination

2018

Related Article: Tao Shu, Long Zhao, Sun Li, Xiang-Yu Chen, Carolina von Essen, Kari Rissanen, Dieter Enders|2018|Angew.Chem.,Int.Ed.|57|10985|doi:10.1002/anie.201806931

Space GroupCrystallographyCrystal System7a'-(4-bromophenyl)-14-diphenyl-3a'7a'-dihydro-2H2'H-spiro[azetidine-33'-[1]benzofuran]-25'(4'H)-dioneCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1437686: Experimental Crystal Structure Determination

2016

Related Article: Tao Shu, Qijian Ni, Xiaoxiao Song, Kun Zhao, Tianyu Wu, Rakesh Puttreddy, Kari Rissanen, Dieter Enders|2016|Chem.Commun.|52|2609|doi:10.1039/C5CC09581F

Space GroupCrystallographyCrystal SystemCrystal Structureethyl 3-(13-benzodioxol-5-yl)-2-(4-chlorophenyl)-4-nitrocyclopentanecarboxylateCell ParametersExperimental 3D Coordinates
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CCDC 1493409: Experimental Crystal Structure Determination

2016

Related Article: Kun Zhao, Ying Zhi, Tao Shu, Arto Valkonen, Kari Rissanen, Dieter Enders|2016|Angew.Chem.,Int.Ed.|55|12104|doi:10.1002/anie.201606947

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1'-t-butyl 2-ethyl 4-(35-di-t-butyl-4-hydroxyphenyl)-5'-iodo-2'-oxo-4H-spiro[chromene-33'-indole]-1'2(2'H)-dicarboxylateExperimental 3D Coordinates
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CCDC 1844760: Experimental Crystal Structure Determination

2018

Related Article: Tao Shu, Sun Li, Xiang-Yu Chen, Qiang Liu, Carolina von Essen, Kari Rissanen, Dieter Enders|2018|Chem.Commun.|54|7661|doi:10.1039/C8CC04145H

Space GroupCrystallographyCrystal SystemCrystal Structuremethyl (4a-methoxy-2-oxo-24a99a-tetrahydro-1H-fluoren-9-yl)acetateCell ParametersExperimental 3D Coordinates
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