Angewandte Chemie International Edition, ISSN 1433-7851, 08/2016, Volume 55, Issue 33, pp. 9788 - 9792
The direct and highly enantioselective synthesis of tetrahydroacridines was achieved through the phosphoric acid catalyzed addition of enamides to in situ...
organocatalysis | asymmetric synthesis | chiral phosphoric acids | ortho-quinone methide imines | nitrogen heterocycles | MUKAIYAMA-ALDOL | AZA-ORTHO-XYLYLENES | ACTIVATION | ASYMMETRIC-SYNTHESIS | DIELS-ALDER REACTIONS | MECHANISM | CARBONYL-COMPOUNDS | CHEMISTRY, MULTIDISCIPLINARY | CYCLOADDITIONS | SUBSTITUTED 1,4-DIHYDROQUINOLINES | GENERATION | Reaction products | Phosphoric acid | Acids | Imines | Quinone | Enantiomers | Chemical synthesis
organocatalysis | asymmetric synthesis | chiral phosphoric acids | ortho-quinone methide imines | nitrogen heterocycles | MUKAIYAMA-ALDOL | AZA-ORTHO-XYLYLENES | ACTIVATION | ASYMMETRIC-SYNTHESIS | DIELS-ALDER REACTIONS | MECHANISM | CARBONYL-COMPOUNDS | CHEMISTRY, MULTIDISCIPLINARY | CYCLOADDITIONS | SUBSTITUTED 1,4-DIHYDROQUINOLINES | GENERATION | Reaction products | Phosphoric acid | Acids | Imines | Quinone | Enantiomers | Chemical synthesis
Journal Article
Advanced Synthesis & Catalysis, ISSN 1615-4150, 11/2018, Volume 360, Issue 21, pp. 4225 - 4235
A catalytic asymmetric [4+2] cyclization of para‐quinone methide (p‐QM) derivatives with 3‐alkyl‐2‐vinylindoles in the presence of a chiral phosphoric acid has...
asymmetric organocatalysis | enantioselectivity | chiral phosphoric acid | cyclization | vinylindole | para-quinone methide | 1,6-CONJUGATE ADDITION | CHEMISTRY, ORGANIC | 3-METHYL-2-VINYLINDOLES | ENANTIOSELECTIVE CONSTRUCTION | ADDITION/AROMATIZATION | PHOSPHORIC-ACID | DIELS-ALDER REACTION | STEREOGENIC CENTERS | SCAFFOLDS | CHEMISTRY, APPLIED | DIHYDROCOUMARINS | COUMARIN DERIVATIVES | Phosphates | Phosphoric acid | Catalysis | Enantiomers | Derivatives (Financial instruments) | Quinone | Derivatives | Asymmetry | Alkenes | Construction methods
asymmetric organocatalysis | enantioselectivity | chiral phosphoric acid | cyclization | vinylindole | para-quinone methide | 1,6-CONJUGATE ADDITION | CHEMISTRY, ORGANIC | 3-METHYL-2-VINYLINDOLES | ENANTIOSELECTIVE CONSTRUCTION | ADDITION/AROMATIZATION | PHOSPHORIC-ACID | DIELS-ALDER REACTION | STEREOGENIC CENTERS | SCAFFOLDS | CHEMISTRY, APPLIED | DIHYDROCOUMARINS | COUMARIN DERIVATIVES | Phosphates | Phosphoric acid | Catalysis | Enantiomers | Derivatives (Financial instruments) | Quinone | Derivatives | Asymmetry | Alkenes | Construction methods
Journal Article
The Journal of Organic Chemistry, ISSN 0022-3263, 02/2018, Volume 83, Issue 3, pp. 1414 - 1421
The first cyclization of para-quinone methide derivatives with alkynes was established by utilizing the [4 + 2] reaction of ortho-hydroxyphenyl-substituted...
CATALYZED ADDITION | ASYMMETRIC 1,6-CONJUGATE ADDITION | ENANTIOSELECTIVE SYNTHESIS | ADDITION/AROMATIZATION | SULFONIUM SALTS | ANNULATION | DIELS-ALDER REACTION | CHEMISTRY, ORGANIC | ACID-ESTERS | SPIROCYCLOPROPANATION | DIHYDROCOUMARINS | Usage | Chemical properties | Cascade reactions | Quinone
CATALYZED ADDITION | ASYMMETRIC 1,6-CONJUGATE ADDITION | ENANTIOSELECTIVE SYNTHESIS | ADDITION/AROMATIZATION | SULFONIUM SALTS | ANNULATION | DIELS-ALDER REACTION | CHEMISTRY, ORGANIC | ACID-ESTERS | SPIROCYCLOPROPANATION | DIHYDROCOUMARINS | Usage | Chemical properties | Cascade reactions | Quinone
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 03/2017, Volume 56, Issue 13, pp. 3689 - 3693
We report herein a dynamic kinetic resolution (DKR) involving ortho‐quinone methide (o‐QM) intermediates. In the presence of Et3N and the cinchonine‐derived...
benzylic sulfones | ortho-quinone methides | cycloaddition | dynamic kinetic resolution | chromans | ANNULATIONS | O-HYDROXYBENZYL ALCOHOLS | BAYLIS-HILLMAN REACTION | CHEMISTRY, MULTIDISCIPLINARY | ALLYLIC SULFONES | HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES | ALLENOATES | BRONSTED ACID CATALYSIS | CATALYTIC ASYMMETRIC-SYNTHESIS | IN-SITU | CONJUGATE ADDITION | Phenols | Sulfur compounds | Enantiomers | Quinone | Organic compounds | Quinones | Catalysts | Chemical reactions | Esters | Substrates | Intermediates
benzylic sulfones | ortho-quinone methides | cycloaddition | dynamic kinetic resolution | chromans | ANNULATIONS | O-HYDROXYBENZYL ALCOHOLS | BAYLIS-HILLMAN REACTION | CHEMISTRY, MULTIDISCIPLINARY | ALLYLIC SULFONES | HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES | ALLENOATES | BRONSTED ACID CATALYSIS | CATALYTIC ASYMMETRIC-SYNTHESIS | IN-SITU | CONJUGATE ADDITION | Phenols | Sulfur compounds | Enantiomers | Quinone | Organic compounds | Quinones | Catalysts | Chemical reactions | Esters | Substrates | Intermediates
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 08/2017, Volume 56, Issue 32, pp. 9527 - 9531
A visible‐light‐driven radical‐mediated strategy for the in situ generation of aza‐ortho‐quinone methides from 2‐vinyl‐substituted anilines and alkyl radical...
aza-ortho-quinone methides | indoles | radicals | photochemistry | sulfur ylides | DONOR-ACCEPTOR COMPLEX | ORGANIC-SYNTHESIS | ORTHO-XYLYLENES | CHEMISTRY, MULTIDISCIPLINARY | PHOTOREDOX CATALYSIS | UNACTIVATED ALKENES | PHOTOCHEMICAL ACTIVITY | FLUOROALKYLATION REACTIONS | METAL-FREE | ANNULATION REACTIONS | Sulfur compounds | Quinone | Cycloaddition | Indoles | Sulfur | Chemical synthesis | Halides
aza-ortho-quinone methides | indoles | radicals | photochemistry | sulfur ylides | DONOR-ACCEPTOR COMPLEX | ORGANIC-SYNTHESIS | ORTHO-XYLYLENES | CHEMISTRY, MULTIDISCIPLINARY | PHOTOREDOX CATALYSIS | UNACTIVATED ALKENES | PHOTOCHEMICAL ACTIVITY | FLUOROALKYLATION REACTIONS | METAL-FREE | ANNULATION REACTIONS | Sulfur compounds | Quinone | Cycloaddition | Indoles | Sulfur | Chemical synthesis | Halides
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 04/2018, Volume 57, Issue 17, pp. 4774 - 4778
Aza‐Diels–Alder reactions (ADARs) are powerful processes that furnish N‐heterocycles in a straightforward fashion. Intramolecular variants offer the additional...
organocatalysis | quinone methide imines | asymmetric synthesis | Brønsted acid catalysis | nitrogen heterocycles | ASYMMETRIC-SYNTHESIS | CARBONYL-COMPOUNDS | HYDROAMINATION/ASYMMETRIC TRANSFER HYDROGENATION | CHEMISTRY, MULTIDISCIPLINARY | RELAY CATALYSIS | ACTIVATION STRATEGY | Bronsted acid catalysis | 4+2 CYCLOADDITION | BETA-DICARBONYLS | N-(ORTHO-CHLOROMETHYL)ARYL AMIDES | IN-SITU | Schiff bases | Synthesis | Catalysis | Enantiomers | Quinone | Organic compounds | Stereoselectivity | Imines | Cascade chemical reactions | Chemical synthesis | Substrates
organocatalysis | quinone methide imines | asymmetric synthesis | Brønsted acid catalysis | nitrogen heterocycles | ASYMMETRIC-SYNTHESIS | CARBONYL-COMPOUNDS | HYDROAMINATION/ASYMMETRIC TRANSFER HYDROGENATION | CHEMISTRY, MULTIDISCIPLINARY | RELAY CATALYSIS | ACTIVATION STRATEGY | Bronsted acid catalysis | 4+2 CYCLOADDITION | BETA-DICARBONYLS | N-(ORTHO-CHLOROMETHYL)ARYL AMIDES | IN-SITU | Schiff bases | Synthesis | Catalysis | Enantiomers | Quinone | Organic compounds | Stereoselectivity | Imines | Cascade chemical reactions | Chemical synthesis | Substrates
Journal Article
ChemCatChem, ISSN 1867-3880, 05/2015, Volume 7, Issue 10, pp. 1524 - 1526
A new sheriff in town: para‐Quinone methides (p‐QMs) have been successfully used in asymmetric organocatalysis. Particularly, the asymmetric 1,6‐addition of...
organocatalysis | quinone methide | 1,6‐addition | asymmetric catalysis | reaction intermediate | Reaction intermediate | Quinone methide | Asymmetric catalysis | Organocatalysis | 1,6-addition | ANNULATIONS | STYRENES | PHENOL | AEROBIC DIALKOXYLATION | ALKYLATION | CHEMISTRY, PHYSICAL | ACTIVATION STRATEGY | BIOSYNTHESIS | 6-addition | Quinone | Catalysis
organocatalysis | quinone methide | 1,6‐addition | asymmetric catalysis | reaction intermediate | Reaction intermediate | Quinone methide | Asymmetric catalysis | Organocatalysis | 1,6-addition | ANNULATIONS | STYRENES | PHENOL | AEROBIC DIALKOXYLATION | ALKYLATION | CHEMISTRY, PHYSICAL | ACTIVATION STRATEGY | BIOSYNTHESIS | 6-addition | Quinone | Catalysis
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 04/2017, Volume 56, Issue 18, pp. 4936 - 4940
Herein, we describe the first catalytic asymmetric intramolecular [4+2] cycloaddition of in situ generated ortho‐quinone methides. In the presence of a...
organocatalysis | cycloadditions | asymmetric catalysis | hetero-Diels–Alder reactions | Brønsted acids | UNSATURATED ALCOHOLS | O-HYDROXYBENZYL ALCOHOLS | ENANTIOSELECTIVE ADDITION | CHEMISTRY, MULTIDISCIPLINARY | PRINS CYCLIZATION | FACILE SYNTHESIS | DIASTEREOSELECTIVE SYNTHESIS | hetero-Diels-Alder reactions | CONFINED BRONSTED ACIDS | DIELS-ALDER REACTION | BENZOFURAN OXIDATIVE DEAROMATIZATION | STEREOSELECTIVE-SYNTHESIS | Bronsted acids | Quinone | Catalysis
organocatalysis | cycloadditions | asymmetric catalysis | hetero-Diels–Alder reactions | Brønsted acids | UNSATURATED ALCOHOLS | O-HYDROXYBENZYL ALCOHOLS | ENANTIOSELECTIVE ADDITION | CHEMISTRY, MULTIDISCIPLINARY | PRINS CYCLIZATION | FACILE SYNTHESIS | DIASTEREOSELECTIVE SYNTHESIS | hetero-Diels-Alder reactions | CONFINED BRONSTED ACIDS | DIELS-ALDER REACTION | BENZOFURAN OXIDATIVE DEAROMATIZATION | STEREOSELECTIVE-SYNTHESIS | Bronsted acids | Quinone | Catalysis
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 07/2012, Volume 18, Issue 30, pp. 9160 - 9173
ortho‐Quinone methides (o‐QMs) are emerging as highly useful intermediates, the inherent reactivity of which can be used in linchpin reactions for the...
natural products | cycloaddition | ortho‐quinone methide | electrocyclic reactions | benzopyran | ortho-quinone methide | BIOMIMETIC SYNTHESIS | ROBUSTADIAL-A | DIELS-ALDER REACTIONS | FORMAL SYNTHESIS | ONE-POT SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | BERKELIC ACID | GENERATION | ENANTIOSELECTIVE TOTAL-SYNTHESIS | CONCISE SYNTHESIS | CYCLIZATION | Benzopyrans - chemistry | Biological Products - chemical synthesis | Biological Products - chemistry | Cyclization | Indolequinones - chemical synthesis | Indolequinones - chemistry | Structure-Activity Relationship | Quinone | Natural products | Strategy | Synthesis (chemistry) | Construction | Synthesis
natural products | cycloaddition | ortho‐quinone methide | electrocyclic reactions | benzopyran | ortho-quinone methide | BIOMIMETIC SYNTHESIS | ROBUSTADIAL-A | DIELS-ALDER REACTIONS | FORMAL SYNTHESIS | ONE-POT SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | BERKELIC ACID | GENERATION | ENANTIOSELECTIVE TOTAL-SYNTHESIS | CONCISE SYNTHESIS | CYCLIZATION | Benzopyrans - chemistry | Biological Products - chemical synthesis | Biological Products - chemistry | Cyclization | Indolequinones - chemical synthesis | Indolequinones - chemistry | Structure-Activity Relationship | Quinone | Natural products | Strategy | Synthesis (chemistry) | Construction | Synthesis
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 05/2017, Volume 23, Issue 27, pp. 6509 - 6513
An unprecedented Rauhut–Currier‐type 1,6‐conjugate addition has been developed. With chiral cyclohexane‐based phosphine‐amide catalyst 3 h, the 1,6‐conjugate...
quinone methide | chiral phosphine | asymmetric catalysis | conjugation | rauhut-currier | MORITA-BAYLIS-HILLMAN | CYSTEINE | THIOUREA-PHOSPHINE | MULTIFUNCTIONAL CHIRAL PHOSPHINE | CHEMISTRY, MULTIDISCIPLINARY | ACTIVATED ALKENES | ORGANOCATALYSTS | MICHAEL CYCLOISOMERIZATION | ESTERS | ALPHA-AMINO-ACID | Catalysis | Enantiomers | Quinone | Cyclohexane | Catalysts | Quinones | Amides
quinone methide | chiral phosphine | asymmetric catalysis | conjugation | rauhut-currier | MORITA-BAYLIS-HILLMAN | CYSTEINE | THIOUREA-PHOSPHINE | MULTIFUNCTIONAL CHIRAL PHOSPHINE | CHEMISTRY, MULTIDISCIPLINARY | ACTIVATED ALKENES | ORGANOCATALYSTS | MICHAEL CYCLOISOMERIZATION | ESTERS | ALPHA-AMINO-ACID | Catalysis | Enantiomers | Quinone | Cyclohexane | Catalysts | Quinones | Amides
Journal Article