
The Chemistry of the Morita-Baylis-Hillman Reaction
by Shi, Min; Wang, Fei-jun; Zhao, Mei-xin; Wei, Yin-
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Summary
Table of Contents
Morita-Baylis-Hillman Reaction | p. 1 |
Introduction | p. 1 |
Mechanism of Morita-Baylis-Hillman Reaction | p. 2 |
Amine-catalyzed Mechanism | p. 2 |
Phosphine-catalyzed Mechanism | p. 5 |
Activated Olefins | p. 8 |
Acrylates | p. 9 |
Acrylonitriles | p. 12 |
Allenes, Acetylenes and Dienes | p. 13 |
Acrylamides | p. 17 |
Acrolein | p. 20 |
¿,ß-Unsatyurated Ketones | p. 20 |
ß-Substituted Activated Olefins | p. 24 |
Nitroalkenes | p. 25 |
Vinyl Sulfones, Vinyl Sulfoxides and Vinyl Sulfonates | p. 26 |
Vinylphosphonates | p. 27 |
Miscellaneous Activated Olefins | p. 27 |
Electrophiles | p. 28 |
Aldehydes | p. 28 |
Ketones | p. 39 |
¿-Keto Esters, ß-Keto Lactones, ß-Keto Lactams and Diketones (ß-Keto Carbonyl Compounds) | p. 41 |
Imines and Iminium Salts | p. 44 |
Other Electrophiles | p. 48 |
Multicomponent One-pot Reaction | p. 49 |
Intramolecular Morita-Baylis-Hillman Reaction | p. 51 |
Ionic Liquid as Reaction Media | p. 61 |
References | p. 69 |
Catalytic Systems for the Morita-Baylis-Hillman Reaction | p. 79 |
Introduction | p. 79 |
Amine-catalyzed System | p. 79 |
Achiral Amine | p. 79 |
Chiral Amine | p. 104 |
Cinchona-derived Catalysts | p. 104 |
Unnatural Tertiary Amines | p. 116 |
Non-natural Tertiary Amine/Thiourea (Phenol) Catalysts | p. 121 |
Phosphine-catalyzed System | p. 122 |
Achiral Phosphine | p. 122 |
Chiral Phosphine | p. 132 |
TiCI4-Lewis Acid Mediated Catalyzed System | p. 146 |
Chalcogenide-Lewis Acid Mediated System | p. 155 |
Chalcogenide-TiCI4 Mediated System | p. 156 |
Chalcogeni de-media ted System in the Presence of Other Lewis Acids | p. 163 |
Substrates Containing a Chalcogenide Group | p. 166 |
p. Co-catalyzed | |
Proline as Co-catalyst | p. 170 |
(Thio)ureas as Co-catalyst | p. 175 |
Other Reagents as Co-catalysts | p. 180 |
Polymer-supported Catalysts for the Morita-Baylis-Hillman Reaction | p. 192 |
References | p. 198 |
Transformations of Functional Groups in Morita-Baylis-Hillman Adducts | p. 209 |
Introduction | p. 209 |
Transformations of an Hydroxy! Group | p. 209 |
Esterification and Etherification | p. 209 |
Halogenation | p. 216 |
Miscellaneous Transformations | p. 221 |
Friedel-Crafts Reaction | p. 222 |
Isomerization | p. 227 |
Heck Reaction | p. 230 |
Hydrogenation | p. 233 |
Diels-Alder Reaction | p. 238 |
Nucleophilic Addition | p. 242 |
Carbon Nucleophiles | p. 242 |
Nitrogen Nucleophiles | p. 260 |
Oxygen Nucleophiles | p. 270 |
Sulfur Nucleophiles | p. 274 |
Phosphorus Nucleophiles | p. 278 |
Other Nucleophiles | p. 280 |
Radical Reactions | p. 284 |
Metathesis Reaction | p. 290 |
Other Transformations | p. 295 |
Epoxidation and Aziridination Reactions | p. 295 |
Michael Addition Reactions | p. 299 |
Miscellaneous | p. 305 |
Conclusions | p. 311 |
References | p. 311 |
Morita-Baylis-Hillman Adducts or Derivatives for the Construction of Cyclic Frameworks | p. 325 |
Introduction | p. 325 |
Synthesis of Cyclic Hydrocarbon Compounds | p. 326 |
Cyclopropane Ring Systems | p. 326 |
Five-membered-ring Carbocyclic Compounds | p. 327 |
Six-membered-ring Carbocyclic Compounds | p. 332 |
Aromatic Compounds | p. 338 |
Bridged Compounds | p. 344 |
Medium-sized-ring Carbocyclic Compounds | p. 350 |
Synthesis of Oxygen-containing Heterocyclic Compounds | p. 353 |
Oxiranes | p. 353 |
b-Lactones | p. 356 |
s-Butyrolactones | p. 356 |
Furan-ring Derivatives | p. 362 |
Pyrans | p. 368 |
Pyran-2-ones | p. 370 |
Coumarin Derivatives | p. 376 |
Medium-sized-ring Oxygen-containing Heterocycles | p. 379 |
Synthesis of Nitrogen-containing Heterocyclic Compounds | p. 382 |
Aziridines | p. 382 |
Azetidines | p. 383 |
b-Lactams | p. 384 |
Pyrrole Derivatives | p. 389 |
Indoles and Indolizines | p. 404 |
Piperidines and Pyridines | p. 408 |
Quinolines | p. 414 |
Medium-sized-ring Nitrogen-containing Heterocycles | p. 428 |
Construction of Nitrogen Heterocycles Containing Two Nitrogen Atoms | p. 438 |
Polyheterocyclic Compounds Containing a Nitrogen Atom | p. 441 |
Synthesis of Other Heterocyclic Compounds | p. 452 |
References | p. 461 |
Application of Morita-Baylis-Hillman Reaction for the Synthesis of Natural Products | p. 485 |
Introduction | p. 485 |
Acaterin | p. 485 |
Analogues of N-Benzoyl-syn-phenylisoserine, (S)-ß-Homoserine and (S)Aspartic Acid | p. 486 |
Asmarines A and B | p. 487 |
Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol | p. 489 |
N-Boc-dolaproine | p. 492 |
Borrelidin | p. 492 |
(2E)-2-Butyloct-2-enal | p. 493 |
Caribenolide I | p. 494 |
Clusianone and Polycyclic Polyprenylated Acylphloroglucinols (PPAPs) | p. 494 |
Cyclic Peptides | p. 497 |
(-)-(Z)-Deoxypukalide | p. 497 |
Diversonol | p. 499 |
Dolichol Analogues | p. 503 |
Dykellic Acid and Gelastatin Analogues | p. 503 |
(+)-Efaroxan | p. 505 |
Epopromycin B | p. 505 |
Eupomatilone 2 | p. 505 |
Fleursandol® | p. 511 |
(+)-Frondosin A | p. 514 |
Furaquinocins | p. 515 |
(+)-Heliotridine and (-)-Retronecine | p. 517 |
Luminacin D | p. 519 |
Mycestericin E | p. 519 |
Oxyisoterihanine | p. 521 |
Phaseolinic Acid | p. 521 |
Pinnatoxin A | p. 523 |
Salinosporamide A and its Analogues | p. 523 |
Selenomilfasartan | p. 525 |
Solanoeclepin A | p. 525 |
Sordarin Core | p. 527 |
(-)-Spinosyn A | p. 530 |
(-)-Spirotryprostatin B | p. 530 |
Syributins and Syringolides, Spyhydrofurans and Secosyrins | p. 532 |
Tacamonine | p. 532 |
Core of Eleutherobin | p. 538 |
Trioxacarcinosides B | p. 538 |
Tubelactomicin | p. 540 |
6-Tuliposide B | p. 542 |
(R)-Umbelactone | p. 543 |
References | p. 543 |
Subject Index | p. 552 |
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