Chirality, ISSN 0899-0042, 05/2011, Volume 23, Issue 5, pp. 397 - 403
A detailed experimental investigation of an aza‐Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid‐derived organocatalysts...
organocatalysis | racemization | aza‐Michael reaction | retro‐aza‐Michael reaction | chirality amplification | aza-Michael reaction | retro-aza-Michael reaction | BRONSTED ACID | CHEMISTRY, ANALYTICAL | ACTIVATION | CHEMISTRY, MEDICINAL | ASYMMETRIC-SYNTHESIS | CHEMISTRY, ORGANIC | AROMATIC-AMINES | ENANTIOSELECTIVE CONJUGATE ADDITION | ENONES | PHARMACOLOGY & PHARMACY | Aza Compounds - chemistry | Catalysis | Stereoisomerism | Cinchona Alkaloids - chemistry | Amplification | Stereoselectivity | Solvents | Reproduction | Aniline | Chirality | Racemization | Functional groups
organocatalysis | racemization | aza‐Michael reaction | retro‐aza‐Michael reaction | chirality amplification | aza-Michael reaction | retro-aza-Michael reaction | BRONSTED ACID | CHEMISTRY, ANALYTICAL | ACTIVATION | CHEMISTRY, MEDICINAL | ASYMMETRIC-SYNTHESIS | CHEMISTRY, ORGANIC | AROMATIC-AMINES | ENANTIOSELECTIVE CONJUGATE ADDITION | ENONES | PHARMACOLOGY & PHARMACY | Aza Compounds - chemistry | Catalysis | Stereoisomerism | Cinchona Alkaloids - chemistry | Amplification | Stereoselectivity | Solvents | Reproduction | Aniline | Chirality | Racemization | Functional groups
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 01/2013, Volume 52, Issue 3, pp. 943 - 947
Bifunctional phosphines derived from amino acids mediate the asymmetric Michael addition of 3‐substituted oxindoles to activated alkenes (see scheme)....
Michael addition | oxindoles | alkenes | bifunctional phosphines | amino acids | MORITA-BAYLIS-HILLMAN | DIPEPTIDE-DERIVED PHOSPHINES | RACEMIC CARBOXYLIC-ACIDS | FUNCTIONALIZED CYCLOPENTENES | CHEMISTRY, MULTIDISCIPLINARY | 3+2 ANNULATION | SELECTIVE MANNICH REACTIONS | FEIST-BENARY REACTION | KINETIC RESOLUTION | ELECTRON-DEFICIENT OLEFINS | ACTIVATED OLEFINS | Amino Acids - chemistry | Alkenes - chemistry | Phosphines - chemistry | Catalysis | Stereoisomerism | Indoles - chemistry | Energy conservation | Olefins | Activated | Amino acids | Asymmetry | Alkenes | Michael reaction | Phosphines
Michael addition | oxindoles | alkenes | bifunctional phosphines | amino acids | MORITA-BAYLIS-HILLMAN | DIPEPTIDE-DERIVED PHOSPHINES | RACEMIC CARBOXYLIC-ACIDS | FUNCTIONALIZED CYCLOPENTENES | CHEMISTRY, MULTIDISCIPLINARY | 3+2 ANNULATION | SELECTIVE MANNICH REACTIONS | FEIST-BENARY REACTION | KINETIC RESOLUTION | ELECTRON-DEFICIENT OLEFINS | ACTIVATED OLEFINS | Amino Acids - chemistry | Alkenes - chemistry | Phosphines - chemistry | Catalysis | Stereoisomerism | Indoles - chemistry | Energy conservation | Olefins | Activated | Amino acids | Asymmetry | Alkenes | Michael reaction | Phosphines
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 10/2017, Volume 56, Issue 44, pp. 13612 - 13617
Orthogonal maleimide and thiol deprotections were combined with thiol–maleimide coupling to synthesize discrete oligomers/macromolecules on a gram scale with...
iterative growth | Michael-type additions | dendrimers | discrete oligomers | thiol–maleimide | POLYMERS | CONVERGENT APPROACH | thiol-maleimide | EXPONENTIAL-GROWTH | CHEMISTRY, MULTIDISCIPLINARY | RAPID ROUTE | GLASS-TRANSITION | MODULAR APPROACH | MOLECULAR LENGTH | AMINO-ACIDS | CONJUGATED OLIGOMERS | Oligomers | Polymerization | Dendrimers | Thiols | Coupling (molecular) | Growth rate | Macromolecules | Construction methods | Topology | Degree of polymerization | Chemical synthesis
iterative growth | Michael-type additions | dendrimers | discrete oligomers | thiol–maleimide | POLYMERS | CONVERGENT APPROACH | thiol-maleimide | EXPONENTIAL-GROWTH | CHEMISTRY, MULTIDISCIPLINARY | RAPID ROUTE | GLASS-TRANSITION | MODULAR APPROACH | MOLECULAR LENGTH | AMINO-ACIDS | CONJUGATED OLIGOMERS | Oligomers | Polymerization | Dendrimers | Thiols | Coupling (molecular) | Growth rate | Macromolecules | Construction methods | Topology | Degree of polymerization | Chemical synthesis
Journal Article
JOURNAL OF ORGANIC CHEMISTRY, ISSN 0022-3263, 04/2019, Volume 84, Issue 7, pp. 4381 - 4391
An organocatalyzed dearomative aza-Michael/Michael addition cascade of 2-nitrobenzofurans and 2-nitrobenzothiophenes with 2-aminochalcones has been developed,...
ENANTIOSELECTIVE SYNTHESIS | ANNULATION | 3-ISOTHIOCYANATO OXINDOLES | CONSTRUCTION | 3+2 CYCLOADDITION REACTION | CHEMISTRY, ORGANIC | BISINDOLE ALKALOIDS | 3-NITROINDOLES | ACCESS | MICHAEL ADDITION | N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES
ENANTIOSELECTIVE SYNTHESIS | ANNULATION | 3-ISOTHIOCYANATO OXINDOLES | CONSTRUCTION | 3+2 CYCLOADDITION REACTION | CHEMISTRY, ORGANIC | BISINDOLE ALKALOIDS | 3-NITROINDOLES | ACCESS | MICHAEL ADDITION | N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES
Journal Article
Organic Letters, ISSN 1523-7060, 07/2006, Volume 8, Issue 14, pp. 2901 - 2904
Asymmetric Michael additions of cyclohexanone to both aryl and alkyl nitroolefins in the presence of 20 mol % of organocatalyst 2b and 10 mol % of n-butyric...
HYDROGEN-BOND DONORS | BETA-NITROSTYRENES | PRACTICAL SYNTHESIS | DIELS-ALDER REACTIONS | MANNICH REACTIONS | ASYMMETRIC STRECKER REACTION | BAYLIS-HILLMAN REACTION | CHEMISTRY, ORGANIC | ALDOL REACTIONS | CARBONYL-COMPOUNDS | NITRO-OLEFINS | Alkenes - chemistry | Cyclohexanones - chemistry | Stereoisomerism | Nitro Compounds - chemistry | Molecular Structure | Catalysis | Thiourea - chemistry | Pyrrolidines - chemistry
HYDROGEN-BOND DONORS | BETA-NITROSTYRENES | PRACTICAL SYNTHESIS | DIELS-ALDER REACTIONS | MANNICH REACTIONS | ASYMMETRIC STRECKER REACTION | BAYLIS-HILLMAN REACTION | CHEMISTRY, ORGANIC | ALDOL REACTIONS | CARBONYL-COMPOUNDS | NITRO-OLEFINS | Alkenes - chemistry | Cyclohexanones - chemistry | Stereoisomerism | Nitro Compounds - chemistry | Molecular Structure | Catalysis | Thiourea - chemistry | Pyrrolidines - chemistry
Journal Article
Chemical science, ISSN 2041-6520, 07/2015, Volume 6, Issue 7, pp. 4184 - 4189
We report the first asymmetric sulfa-Michael addition (SMA) reactions using a chiral -heterocyclic carbene (NHC) as a non-covalent organocatalyst. We...
Journal Article
The Journal of Organic Chemistry, ISSN 0022-3263, 02/2015, Volume 80, Issue 3, pp. 1985 - 1992
A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was...
ALDOL | LACTAM | BUTENOLIDES | ISATINS | AMINO | CHEMISTRY, ORGANIC | MANNICH-TYPE | Acrylates - chemistry | Stereoisomerism | Crystallography, X-Ray | Molecular Structure | Butyrophenones - chemistry | Catalysis | Ethylenes - chemistry | Lactams - chemistry | Acrylates | Addition | Chemical properties | Research | Ethylene
ALDOL | LACTAM | BUTENOLIDES | ISATINS | AMINO | CHEMISTRY, ORGANIC | MANNICH-TYPE | Acrylates - chemistry | Stereoisomerism | Crystallography, X-Ray | Molecular Structure | Butyrophenones - chemistry | Catalysis | Ethylenes - chemistry | Lactams - chemistry | Acrylates | Addition | Chemical properties | Research | Ethylene
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 08/2015, Volume 21, Issue 34, pp. 11994 - 11998
A new highly enantioselective domino Michael/hemiketalization reaction of α‐hydroxyacetophenone with β,γ‐unsaturated α‐keto esters for the synthesis of...
asymmetric catalysis | domino reactions | tetrahydrofuran | zinc | Michael/hemiacetalization reactions | ASYMMETRIC CONJUGATE ADDITION | BETA,GAMMA-UNSATURATED ALPHA-KETOESTERS | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION | KETO ESTERS | TERTIARY AMINE CATALYSTS | RING-CLOSING METATHESIS | FEIST-BENARY REACTIONS | HYDROXY-CIS-ALKENES | Michael | ENE-TYPE CYCLIZATION | hemiacetalization reactions | CYCLIC 1,3-DICARBONYL COMPOUNDS | Enantiomers | Furans | Catalysis | Synthesis (chemistry) | Tetrahydrofuran | Optical activity | Strategy | Esters | Ligands | Transformations | Ethers
asymmetric catalysis | domino reactions | tetrahydrofuran | zinc | Michael/hemiacetalization reactions | ASYMMETRIC CONJUGATE ADDITION | BETA,GAMMA-UNSATURATED ALPHA-KETOESTERS | CHEMISTRY, MULTIDISCIPLINARY | MICHAEL ADDITION | KETO ESTERS | TERTIARY AMINE CATALYSTS | RING-CLOSING METATHESIS | FEIST-BENARY REACTIONS | HYDROXY-CIS-ALKENES | Michael | ENE-TYPE CYCLIZATION | hemiacetalization reactions | CYCLIC 1,3-DICARBONYL COMPOUNDS | Enantiomers | Furans | Catalysis | Synthesis (chemistry) | Tetrahydrofuran | Optical activity | Strategy | Esters | Ligands | Transformations | Ethers
Journal Article
Tetrahedron, ISSN 0040-4020, 09/2014, Volume 70, Issue 35, pp. 5468 - 5474
The dinuclear zinc–ProPhenol complex is applied as efficient catalyst in the highly stereoselective tandem Michael addition/acetalization reactions of cyclic...
Michael addition | Oxygen heterocycles | Tandem reaction | Asymmetric catalysis | Dinuclear zinc complex | ENANTIOSELECTIVE SYNTHESIS | 1,3-DICARBONYL COMPOUNDS | BOND-FORMING REACTIONS | CHEMISTRY, ORGANIC | 6-MEMBERED OXYGENATED HETEROCYCLES | KETO ESTERS | ALPHA,BETA-UNSATURATED N-ACYLPYRROLES | PHOSPHINE OXIDES | CONJUGATE ADDITIONS | DERIVATIVES | NITROALKENES | Diketones | Asymmetry | Catalysts | Tetrahedrons | Derivatives | Michael reaction | Zinc
Michael addition | Oxygen heterocycles | Tandem reaction | Asymmetric catalysis | Dinuclear zinc complex | ENANTIOSELECTIVE SYNTHESIS | 1,3-DICARBONYL COMPOUNDS | BOND-FORMING REACTIONS | CHEMISTRY, ORGANIC | 6-MEMBERED OXYGENATED HETEROCYCLES | KETO ESTERS | ALPHA,BETA-UNSATURATED N-ACYLPYRROLES | PHOSPHINE OXIDES | CONJUGATE ADDITIONS | DERIVATIVES | NITROALKENES | Diketones | Asymmetry | Catalysts | Tetrahedrons | Derivatives | Michael reaction | Zinc
Journal Article
Chemical Science, ISSN 2041-6520, 07/2015, Volume 6, Issue 7, pp. 4184 - 4189
We report the first asymmetric sulfa-Michael addition (SMA) reactions using a chiral N-heterocyclic carbene (NHC) as a non-covalent organocatalyst. We...
THIOACETIC ACID | DOMINO REACTIONS | ASYMMETRIC CONJUGATE ADDITION | ALPHA,BETA-UNSATURATED KETONES | 4+2 CYCLOADDITION | KINETIC RESOLUTION | FREE-ENERGY RELATIONSHIPS | BOND-FORMING REACTIONS | SUBSTITUENT CONSTANTS | CHEMISTRY, MULTIDISCIPLINARY | CARBON ACID PK(A)
THIOACETIC ACID | DOMINO REACTIONS | ASYMMETRIC CONJUGATE ADDITION | ALPHA,BETA-UNSATURATED KETONES | 4+2 CYCLOADDITION | KINETIC RESOLUTION | FREE-ENERGY RELATIONSHIPS | BOND-FORMING REACTIONS | SUBSTITUENT CONSTANTS | CHEMISTRY, MULTIDISCIPLINARY | CARBON ACID PK(A)
Journal Article
Tetrahedron, ISSN 0040-4020, 12/2018, Volume 74, Issue 49, pp. 6993 - 6999
A novel [4 + 1] cycloaddition protocol for the synthesis of dihydrobenzo(naphtho)furan skeletons from readily available 2-(2-nitrovinyl)-phen(naphth)ols and...
Dihydrobenzofurans | Nitroalkenes | Iodine-catalyzed | Malonate esters | CELLS | ACID | AZOMETHINE YLIDES | 2,3-DIHYDROBENZOFURANS | CHEMISTRY, ORGANIC | BOND FORMATION | ALLENES | AMINATION | CONSTRUCTION | INHIBITORS | CYCLIZATION
Dihydrobenzofurans | Nitroalkenes | Iodine-catalyzed | Malonate esters | CELLS | ACID | AZOMETHINE YLIDES | 2,3-DIHYDROBENZOFURANS | CHEMISTRY, ORGANIC | BOND FORMATION | ALLENES | AMINATION | CONSTRUCTION | INHIBITORS | CYCLIZATION
Journal Article
European Journal of Organic Chemistry, ISSN 1434-193X, 05/2014, Volume 2014, Issue 15, pp. 3104 - 3107
An unexpected and efficient domino reaction of N‐sulfonyl‐1‐aza‐1,3‐dienes with 2‐halo‐1,3‐dicarbonyl compounds to synthesize differently substituted...
Michael addition | Domino reactions | Oxygen heterocycles | Reaction mechanisms | ONE-POT SYNTHESIS | MANGANESE(III) ACETATE | EFFICIENT SYNTHESIS | CHEMISTRY, ORGANIC | RADICAL SYNTHESIS | HETEROCYCLES | CYCLOADDITIONS | CONSTRUCTION | SUBSTITUTED DIHYDROFURANS | ROCAGLAMIDE | CYCLIZATION | Chemotherapy | Catalysis | Cancer
Michael addition | Domino reactions | Oxygen heterocycles | Reaction mechanisms | ONE-POT SYNTHESIS | MANGANESE(III) ACETATE | EFFICIENT SYNTHESIS | CHEMISTRY, ORGANIC | RADICAL SYNTHESIS | HETEROCYCLES | CYCLOADDITIONS | CONSTRUCTION | SUBSTITUTED DIHYDROFURANS | ROCAGLAMIDE | CYCLIZATION | Chemotherapy | Catalysis | Cancer
Journal Article
ORGANIC LETTERS, ISSN 1523-7060, 09/2009, Volume 11, Issue 17, pp. 3946 - 3949
An atom-economic organocatalytic asymmetric Michael reaction of alpha,beta,beta-trisubstituted olefins has been successfully developed. The reaction exhibits...
BETA-AMINO ACIDS | ALPHA,BETA-UNSATURATED KETONES | THIOUREA ORGANOCATALYSTS | CHEMISTRY, ORGANIC | ASYMMETRIC CONJUGATE ADDITIONS | DIALKYLZINC REAGENTS | BIFUNCTIONAL CINCHONA ORGANOCATALYSTS | STEREOGENIC CENTERS | STEREOSELECTIVE-SYNTHESIS | ARYL ALUMINUM REAGENTS | Alkenes - chemistry | Combinatorial Chemistry Techniques | Peptides - chemical synthesis | Peptides - chemistry | Stereoisomerism | Nitro Compounds - chemistry | Amino Acids - chemistry | Molecular Structure | Amino Acids - chemical synthesis | Catalysis
BETA-AMINO ACIDS | ALPHA,BETA-UNSATURATED KETONES | THIOUREA ORGANOCATALYSTS | CHEMISTRY, ORGANIC | ASYMMETRIC CONJUGATE ADDITIONS | DIALKYLZINC REAGENTS | BIFUNCTIONAL CINCHONA ORGANOCATALYSTS | STEREOGENIC CENTERS | STEREOSELECTIVE-SYNTHESIS | ARYL ALUMINUM REAGENTS | Alkenes - chemistry | Combinatorial Chemistry Techniques | Peptides - chemical synthesis | Peptides - chemistry | Stereoisomerism | Nitro Compounds - chemistry | Amino Acids - chemistry | Molecular Structure | Amino Acids - chemical synthesis | Catalysis
Journal Article
ACS CATALYSIS, ISSN 2155-5435, 09/2019, Volume 9, Issue 9, pp. 8693 - 8701
The development of a switchable strategy to control the catalytic action of dual active species is of great significance toward the precise manipulation of a...
ALDOL | ASYMMETRIC TRANSFER HYDROGENATION | immobilization | SHELL | PERIODIC MESOPOROUS ORGANOSILICA | silica | COMPLEXES | CHEMISTRY, PHYSICAL | HETEROGENEOUS CATALYSIS | asymmetric catalysis | mesoporous material | heterogeneous catalyst | KETONES | NANOREACTOR | CHIRAL CATALYSTS
ALDOL | ASYMMETRIC TRANSFER HYDROGENATION | immobilization | SHELL | PERIODIC MESOPOROUS ORGANOSILICA | silica | COMPLEXES | CHEMISTRY, PHYSICAL | HETEROGENEOUS CATALYSIS | asymmetric catalysis | mesoporous material | heterogeneous catalyst | KETONES | NANOREACTOR | CHIRAL CATALYSTS
Journal Article