Advanced Synthesis & Catalysis, ISSN 1615-4150, 12/2017, Volume 359, Issue 23, pp. 4136 - 4140
An efficient enantioselective vinylogous aldol reaction of 3‐alkylidene oxindoles with α‐ketoesters by a bifunctional thiourea catalyst derived from cinchona...
Aldol reaction | α-Ketoesters | Vinylogous reaction | Organocatalysis | 3-Alkylidene oxindoles | ORGANIC-SYNTHESIS | CATALYSIS | ACTIVATION | alpha-Ketoesters | MUKAIYAMA 1,6-MICHAEL/MICHAEL ADDITION | CHEMISTRY, ORGANIC | MICHAEL ADDITION | MANNICH REACTION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | UNSATURATED BUTYROLACTONES | LEWIS-ACIDS | CHEMISTRY, APPLIED | CONJUGATE ADDITION
Aldol reaction | α-Ketoesters | Vinylogous reaction | Organocatalysis | 3-Alkylidene oxindoles | ORGANIC-SYNTHESIS | CATALYSIS | ACTIVATION | alpha-Ketoesters | MUKAIYAMA 1,6-MICHAEL/MICHAEL ADDITION | CHEMISTRY, ORGANIC | MICHAEL ADDITION | MANNICH REACTION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | UNSATURATED BUTYROLACTONES | LEWIS-ACIDS | CHEMISTRY, APPLIED | CONJUGATE ADDITION
Journal Article
Advanced Synthesis & Catalysis, ISSN 1615-4150, 11/2015, Volume 357, Issue 16‐17, pp. 3507 - 3511
The first direct and enantioselective vinylogous Michael/cyclization cascade reaction between acyclic β,γ‐unsaturated amides and isatylidene malononitriles has...
spirocyclic oxindoles | enantioselective organocatalysis | cascade reaction | cyclization | vinylogous Michael reaction | CATALYSIS | BAYLIS-HILLMAN REACTION | CHEMISTRY, ORGANIC | ALDEHYDES | BUTENOLIDE | PYRAZOLEAMIDES | MICHAEL ADDITION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | spirocyclic oxindoles: vinylogous Michael reaction | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES | CONJUGATE ADDITION | ACRYLATES | Construction | Synthesis | Asymmetry | Optical activity | Amides | Malononitrile | Cascade chemical reactions | Catalysis
spirocyclic oxindoles | enantioselective organocatalysis | cascade reaction | cyclization | vinylogous Michael reaction | CATALYSIS | BAYLIS-HILLMAN REACTION | CHEMISTRY, ORGANIC | ALDEHYDES | BUTENOLIDE | PYRAZOLEAMIDES | MICHAEL ADDITION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | spirocyclic oxindoles: vinylogous Michael reaction | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES | CONJUGATE ADDITION | ACRYLATES | Construction | Synthesis | Asymmetry | Optical activity | Amides | Malononitrile | Cascade chemical reactions | Catalysis
Journal Article
Molecules, ISSN 1420-3049, 10/2017, Volume 22, Issue 10, p. 1636
The ubiquitous presence of spirooxindole architectures with several functionalities and stereogenic centers in bioactive molecules has been appealing for the...
Domino | Chiral building blocks | Hydrogen-bonding | Enantioselectivity | Non-covalent organocatalysis | Spirooxindole derivatives | Tandem | Cascade | enantioselectivity | ENANTIOSELECTIVE SYNTHESIS | cascade | BIOCHEMISTRY & MOLECULAR BIOLOGY | 3-ISOTHIOCYANATO OXINDOLES | CONTIGUOUS STEREOCENTERS | SPIROCYCLIC OXINDOLES | QUATERNARY CENTERS | CHEMISTRY, MULTIDISCIPLINARY | spirooxindole derivatives | hydrogen-bonding | MICHAEL-CYCLIZATION | MULTIPLE STEREOCENTERS | tandem | non-covalent organocatalysis | MICHAEL/CYCLIZATION CASCADE REACTION | domino | chiral building blocks | 3-ALKYLIDENE OXINDOLES | CATALYTIC ASYMMETRIC-SYNTHESIS | Chemistry Techniques, Synthetic | Hydrogen Bonding | Stereoisomerism | Spiro Compounds - chemical synthesis | Indoles - chemical synthesis | Molecular Structure | Catalysis | Indoles - chemistry | Cinchona Alkaloids - chemistry | Spiro Compounds - chemistry | State-of-the-art reviews | Cascade chemical reactions | Organic chemistry | Chemical Sciences
Domino | Chiral building blocks | Hydrogen-bonding | Enantioselectivity | Non-covalent organocatalysis | Spirooxindole derivatives | Tandem | Cascade | enantioselectivity | ENANTIOSELECTIVE SYNTHESIS | cascade | BIOCHEMISTRY & MOLECULAR BIOLOGY | 3-ISOTHIOCYANATO OXINDOLES | CONTIGUOUS STEREOCENTERS | SPIROCYCLIC OXINDOLES | QUATERNARY CENTERS | CHEMISTRY, MULTIDISCIPLINARY | spirooxindole derivatives | hydrogen-bonding | MICHAEL-CYCLIZATION | MULTIPLE STEREOCENTERS | tandem | non-covalent organocatalysis | MICHAEL/CYCLIZATION CASCADE REACTION | domino | chiral building blocks | 3-ALKYLIDENE OXINDOLES | CATALYTIC ASYMMETRIC-SYNTHESIS | Chemistry Techniques, Synthetic | Hydrogen Bonding | Stereoisomerism | Spiro Compounds - chemical synthesis | Indoles - chemical synthesis | Molecular Structure | Catalysis | Indoles - chemistry | Cinchona Alkaloids - chemistry | Spiro Compounds - chemistry | State-of-the-art reviews | Cascade chemical reactions | Organic chemistry | Chemical Sciences
Journal Article
RSC Advances, ISSN 2046-2069, 2018, Volume 8, Issue 58, pp. 33451 - 33458
A novel vinylogous aldol addition of alkylidene oxindole with 1-trifluoromethyl-3-alkylidene-propan-2-ones is presented. The reaction, catalyzed by a...
CINCHONA ALKALOIDS | CATALYSIS | TERTIARY ALCOHOLS | DIELS-ALDER REACTIONS | CONSTRUCTION | CARBONYL-COMPOUNDS | FLUORINATION | 3-ALKYLIDENE OXINDOLES | TRIFLUOROMETHYL KETONES | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION
CINCHONA ALKALOIDS | CATALYSIS | TERTIARY ALCOHOLS | DIELS-ALDER REACTIONS | CONSTRUCTION | CARBONYL-COMPOUNDS | FLUORINATION | 3-ALKYLIDENE OXINDOLES | TRIFLUOROMETHYL KETONES | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION
Journal Article
Heteroatom Chemistry, ISSN 1042-7163, 03/2018, Volume 29, Issue 2, pp. e21416 - n/a
A facile and efficient synthesis of 2‐oxindole derivatives bearing tetrahydropyrazine scaffold has been developed. Using water as solvent without any...
pyrazine | catalyst free | water | 2‐oxindole | 3‐alkylidene‐oxindoles | 3-alkylidene-oxindoles | 2-oxindole | INHIBITORS | OXINDOLE | CHEMISTRY, MULTIDISCIPLINARY | ACCESS
pyrazine | catalyst free | water | 2‐oxindole | 3‐alkylidene‐oxindoles | 3-alkylidene-oxindoles | 2-oxindole | INHIBITORS | OXINDOLE | CHEMISTRY, MULTIDISCIPLINARY | ACCESS
Journal Article
CHEMICAL COMMUNICATIONS, ISSN 1359-7345, 08/2019, Volume 55, Issue 63, pp. 9327 - 9330
A highly stereoselective sequential vinylogous aldol reaction/transesterification of methyl-substituted olefinic butyrolactones and isatins was developed. With...
MANNICH REACTION | KETONES | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | ASYMMETRIC-SYNTHESIS | CYCLIZATION CASCADE REACTION | DIELS-ALDER REACTION | 3-ALKYLIDENE OXINDOLES | CHEMISTRY, MULTIDISCIPLINARY | 3+2 CYCLOADDITION | ACCESS | MICHAEL ADDITION
MANNICH REACTION | KETONES | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | ASYMMETRIC-SYNTHESIS | CYCLIZATION CASCADE REACTION | DIELS-ALDER REACTION | 3-ALKYLIDENE OXINDOLES | CHEMISTRY, MULTIDISCIPLINARY | 3+2 CYCLOADDITION | ACCESS | MICHAEL ADDITION
Journal Article
Advanced Synthesis & Catalysis, ISSN 1615-4150, 02/2018, Volume 360, Issue 4, pp. 711 - 721
We introduce 3‐(alkoxycarbonyl‐2‐alkyliden)‐2‐oxindoles as pronucleophilic donors in the direct, vinylogous Michael addition to nitroolefins orchestrated by a...
organocatalysis | oxindoles | density functional calculations | asymmetric catalysis | vinylogous Michael reaction | REACTIVITY | CHEMISTRY, ORGANIC | 3-(2-OXOINDOLIN-3-YLIDENE)BUTANOATES | ASYMMETRIC TRANSFORMATIONS | MUKAIYAMA ALDOL REACTIONS | THIOUREA ORGANOCATALYSTS | CONSTRUCTION | CHEMISTRY | STEREOSELECTIVE-SYNTHESIS | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES | 1,2-DICARBONYL COMPOUNDS | Proline | Catalysis | Catalysts | Adducts
organocatalysis | oxindoles | density functional calculations | asymmetric catalysis | vinylogous Michael reaction | REACTIVITY | CHEMISTRY, ORGANIC | 3-(2-OXOINDOLIN-3-YLIDENE)BUTANOATES | ASYMMETRIC TRANSFORMATIONS | MUKAIYAMA ALDOL REACTIONS | THIOUREA ORGANOCATALYSTS | CONSTRUCTION | CHEMISTRY | STEREOSELECTIVE-SYNTHESIS | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES | 1,2-DICARBONYL COMPOUNDS | Proline | Catalysis | Catalysts | Adducts
Journal Article
Advanced Synthesis & Catalysis, ISSN 1615-4150, 11/2017, Volume 359, Issue 22, pp. 4043 - 4049
A highly region‐, diastereo‐, and enantioselective organocatalytic vinylogous aldol‐cyclization cascade reaction of prochiral 3‐akylidene oxindoles to isatins...
Organocatalysis | 3-Akylidene oxindoles | Spirooxindole δ-lactones | Vinylogous aldol−cyclization | CATALYSIS | 1,3-DIPOLAR CYCLOADDITIONS | ACTIVATION | SPIROCYCLIC OXINDOLE-DIHYDROPYRANONES | THIOUREA | ALLYLIC ALKYLATION | CHEMISTRY, ORGANIC | MICHAEL ADDITION | Spirooxindole delta-lactones | Vinylogous aldol - cyclization | ISATINS | FACILE CONSTRUCTION | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES
Organocatalysis | 3-Akylidene oxindoles | Spirooxindole δ-lactones | Vinylogous aldol−cyclization | CATALYSIS | 1,3-DIPOLAR CYCLOADDITIONS | ACTIVATION | SPIROCYCLIC OXINDOLE-DIHYDROPYRANONES | THIOUREA | ALLYLIC ALKYLATION | CHEMISTRY, ORGANIC | MICHAEL ADDITION | Spirooxindole delta-lactones | Vinylogous aldol - cyclization | ISATINS | FACILE CONSTRUCTION | CHEMISTRY, APPLIED | 3-ALKYLIDENE OXINDOLES
Journal Article
Chemical Communications, ISSN 1359-7345, 2019, Volume 55, Issue 10, pp. 1398 - 1401
An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex...
ASYMMETRIC-SYNTHESIS | 3-ALKYLIDENE OXINDOLES | PRODUCTS | CHEMISTRY, MULTIDISCIPLINARY | CONSTRUCTION | ACRYLATES
ASYMMETRIC-SYNTHESIS | 3-ALKYLIDENE OXINDOLES | PRODUCTS | CHEMISTRY, MULTIDISCIPLINARY | CONSTRUCTION | ACRYLATES
Journal Article
The Journal of Organic Chemistry, ISSN 0022-3263, 10/2018, Volume 83, Issue 20, pp. 12440 - 12448
The novel vinylogous aldol-lactonization cascade of alkylidene oxindole with trifluoromethyl ketones is presented. The reaction, catalyzed by a bifunctional...
FUNCTIONALIZATION | KETONES | ASYMMETRIC-SYNTHESIS | DISCODERMOLIDE | CONSTRUCTION | REACTIVITY | CHEMISTRY, ORGANIC | REGIO | 3-ALKYLIDENE OXINDOLES | MICHAEL ADDITION | ENALS
FUNCTIONALIZATION | KETONES | ASYMMETRIC-SYNTHESIS | DISCODERMOLIDE | CONSTRUCTION | REACTIVITY | CHEMISTRY, ORGANIC | REGIO | 3-ALKYLIDENE OXINDOLES | MICHAEL ADDITION | ENALS
Journal Article
Organic Letters, ISSN 1523-7060, 12/2017, Volume 19, Issue 24, pp. 6708 - 6711
A highly diastereoselective vinylogous nucleophilic 1,6-conjugate addition reaction of para-quinone methides with 3-propenyl-2-silyloxyindoles by a bismuth...
DECONJUGATED BUTENOLIDES | ASYMMETRIC-SYNTHESIS | DIELS-ALDER REACTIONS | PHOSPHORIC-ACID | MANNICH REACTIONS | NITROOLEFINS | CHEMISTRY, ORGANIC | STEREOGENIC CENTERS | 3-ALKYLIDENE OXINDOLES | ENANTIOSELECTIVE CONSTRUCTION | MICHAEL ADDITION
DECONJUGATED BUTENOLIDES | ASYMMETRIC-SYNTHESIS | DIELS-ALDER REACTIONS | PHOSPHORIC-ACID | MANNICH REACTIONS | NITROOLEFINS | CHEMISTRY, ORGANIC | STEREOGENIC CENTERS | 3-ALKYLIDENE OXINDOLES | ENANTIOSELECTIVE CONSTRUCTION | MICHAEL ADDITION
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 04/2015, Volume 21, Issue 17, pp. 6433 - 6442
The first example of catalytic, enantioselective hypervinylogous Mukaiyama aldol reaction (HVMAR) involving multiply unsaturated 2‐silyloxyindoles is reported....
oxindoles | aldol reaction | amides | vinylogy | asymmetric synthesis | Amides | Oxindoles | Aldol reaction | Asymmetric synthesis | Vinylogy | ACIDS | LEWIS-BASE ACTIVATION | 3-ALKYLIDENE OXINDOLES | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION | Synthesis | Enantiomers | Aldehydes | Analysis | Organic compounds | Catalysts | Pushing | Olefins | Unsaturated | Selectivity | Boundaries | Catalysis
oxindoles | aldol reaction | amides | vinylogy | asymmetric synthesis | Amides | Oxindoles | Aldol reaction | Asymmetric synthesis | Vinylogy | ACIDS | LEWIS-BASE ACTIVATION | 3-ALKYLIDENE OXINDOLES | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION | Synthesis | Enantiomers | Aldehydes | Analysis | Organic compounds | Catalysts | Pushing | Olefins | Unsaturated | Selectivity | Boundaries | Catalysis
Journal Article
Chemical communications (Cambridge, England), ISSN 1359-7345, 03/2016, Volume 52, Issue 20, pp. 3943 - 3946
An unprecedented sequential gold-catalyzed enone-formation and bifunctional tertiary amine mediated asymmetric cyanosilylation reaction is developed, allowing...
Journal Article
Organic Letters, ISSN 1523-7060, 04/2017, Volume 19, Issue 8, pp. 2130 - 2133
A highly enantioselective supramolecular iminium-catalyzed vinylogous Michael addition/Stetter relay sequence has been developed. This transformation provided...
COMPLEX | ASYMMETRIC-SYNTHESIS | ALDOL REACTION | IMINIUM CATALYSIS | CHEMISTRY, ORGANIC | CASCADE | APLYKURODINONE-1 | 3-ALKYLIDENE OXINDOLES | CYCLOPENTENONES | DERIVATIVES | MICHAEL ADDITION
COMPLEX | ASYMMETRIC-SYNTHESIS | ALDOL REACTION | IMINIUM CATALYSIS | CHEMISTRY, ORGANIC | CASCADE | APLYKURODINONE-1 | 3-ALKYLIDENE OXINDOLES | CYCLOPENTENONES | DERIVATIVES | MICHAEL ADDITION
Journal Article
Chemical Communications, ISSN 1359-7345, 2016, Volume 52, Issue 20, pp. 3943 - 3946
An unprecedented sequential gold-catalyzed enone-formation and bifunctional tertiary amine mediated asymmetric cyanosilylation reaction is developed, allowing...
MULTICOMPONENT REACTIONS | COOPERATIVE CATALYSIS | ACID CATALYSIS | CARBENE INSERTION | VINYLOGOUS MICHAEL ADDITION | H BOND FUNCTIONALIZATION | 3-ALKYLIDENE OXINDOLES | ENANTIOSELECTIVE CYANOSILYLATION | 3-COMPONENT REACTIONS | RECYCLE WASTE | CHEMISTRY, MULTIDISCIPLINARY | Synthesis (chemistry) | Amines | Asymmetry | Optical activity | Cyanides | Furans | Catalysis
MULTICOMPONENT REACTIONS | COOPERATIVE CATALYSIS | ACID CATALYSIS | CARBENE INSERTION | VINYLOGOUS MICHAEL ADDITION | H BOND FUNCTIONALIZATION | 3-ALKYLIDENE OXINDOLES | ENANTIOSELECTIVE CYANOSILYLATION | 3-COMPONENT REACTIONS | RECYCLE WASTE | CHEMISTRY, MULTIDISCIPLINARY | Synthesis (chemistry) | Amines | Asymmetry | Optical activity | Cyanides | Furans | Catalysis
Journal Article
Asian Journal of Organic Chemistry, ISSN 2193-5807, 07/2015, Volume 4, Issue 7, pp. 619 - 621
The highly efficient asymmetric vinylogous Michael addition of 3‐(2‐oxoindolin‐3‐ylidene)butanoates to nitroalkenes, catalyzed by a cinchona‐based squaramide,...
squaramides | Michael addition | oxindoles | Cinchona alkaloids | alkenes | Oxindoles | Squaramides | Alkenes | ENANTIOSELECTIVE SYNTHESIS | SUBSTITUTED BUTENOLIDES | CHEMISTRY, ORGANIC | MALONONITRILES | CASCADE REACTION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | MALEIMIDES | ALDOL REACTION | CONSTRUCTION | NITROOLEFINS | 3-ALKYLIDENE OXINDOLES
squaramides | Michael addition | oxindoles | Cinchona alkaloids | alkenes | Oxindoles | Squaramides | Alkenes | ENANTIOSELECTIVE SYNTHESIS | SUBSTITUTED BUTENOLIDES | CHEMISTRY, ORGANIC | MALONONITRILES | CASCADE REACTION | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | MALEIMIDES | ALDOL REACTION | CONSTRUCTION | NITROOLEFINS | 3-ALKYLIDENE OXINDOLES
Journal Article
Organic Letters, ISSN 1523-7060, 02/2016, Volume 18, Issue 4, pp. 688 - 691
An unprecedented organocatalytic enantioselective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted...
CINCHONA ALKALOIDS | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | ALPHA-HYDROXY ESTERS | SUBSTITUTED BUTENOLIDES | QUATERNARY STEREOCENTERS | NITROOLEFINS | CHEMISTRY, ORGANIC | STEREOSELECTIVE-SYNTHESIS | 3-ALKYLIDENE OXINDOLES | ASYMMETRIC HENRY REACTION | BIFUNCTIONAL ORGANOCATALYSTS
CINCHONA ALKALOIDS | ALPHA,BETA-UNSATURATED GAMMA-BUTYROLACTAM | ALPHA-HYDROXY ESTERS | SUBSTITUTED BUTENOLIDES | QUATERNARY STEREOCENTERS | NITROOLEFINS | CHEMISTRY, ORGANIC | STEREOSELECTIVE-SYNTHESIS | 3-ALKYLIDENE OXINDOLES | ASYMMETRIC HENRY REACTION | BIFUNCTIONAL ORGANOCATALYSTS
Journal Article