The Chemistry of the Morita-Baylis-Hillman Reaction / Min Shi, Fei-Jun Wang, Mei-Xin Zhao, Yin Wei.

• 1 Morita–Baylis–Hillman Reaction / Mei-Xin Zhao, Yin Wei and Min Shi -- 1.1 Introduction -- 1.2 Mechanism of Morita–Baylis–Hillman Reaction -- 1.3 Activated Olefins -- 1.4 Electrophiles -- 1.5 Multicomponent One-pot Reaction -- 1.6 Intramolecular Morita–Baylis–Hillman Reaction -- 1.7 Ionic Liquid as Reaction Media -- 2 Catalytic Systems for the Morita–Baylis–Hillman Reaction / Mei-Xin Zhao, Yin Wei and Min Shi -- 2.1 Introduction -- 2.2 Amine-catalyzed System -- 2.3 Phosphine-catalyzed System -- 2.4 TiCl4-Lewis Acid Mediated Catalyzed System -- 2.5 Chalcogenide-Lewis Acid Mediated System -- 2.6 Co-catalyzed Systems -- 2.7 Polymer-supported Catalysts for the Morita–Baylis–Hillman Reaction -- 3 Transformations of Functional Groups in Morita–Baylis–Hillman Adducts / Mei-Xin Zhao, Yin Wei and Min Shi -- 3.1 Introduction -- 3.2 Transformations of an Hydroxyl Group -- 3.3 Friedel–Crafts Reaction -- 3.4 Isomerization -- 3.5 Heck Reaction -- 3.6 Hydrogenation -- 3.7 Diels–Alder Reaction -- 3.8 Nucleophilic Addition -- 3.9 Radical Reactions -- 3.10 Metathesis Reaction -- 3.11 Other Transformations -- 3.12 Conclusions -- 4 Morita–Baylis–Hillman Adducts or Derivatives for the Construction of Cyclic Frameworks / Fei-Jun Wang, Yin Wei and Min Shi -- 4.1 Introduction -- 4.2 Synthesis of Cyclic Hydrocarbon Compounds -- 4.3 Synthesis of Oxygen-containing Heterocyclic Compounds -- 4.4 Synthesis of Nitrogen-containing Heterocyclic Compounds -- 4.5 Synthesis of Other Heterocyclic Compounds. 
• 5 Application of Morita–Baylis–Hillman Reaction for the Synthesis of Natural Products / Fei-Jun Wang, Yin Wei and Min Shi -- 5.1 Introduction -- 5.2 Acaterin -- 5.3 Analogues of N-Benzoyl-syn-phenylisoserine, (S)-b-Homoserine and (S)-Aspartic Acid -- 5.4 Asmarines A and B -- 5.5 Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol -- 5.6 N-Boc-dolaproine -- 5.7 Borrelidin -- 5.8 (2E)-2-Butyloct-2-enal -- 5.9 Caribenolide I -- 5.10 Clusianone and Polycyclic Polyprenylated Acylphloroglucinols (PPAPs) -- 5.11 Cyclic Peptides -- 5.12 (–)-(Z)-Deoxypukalide -- 5.13 Diversonol -- 5.14 Dolichol Analogues -- 5.15 Dykellic Acid and Gelastatin Analogues -- 5.16 (+)-Efaroxan -- 5.17 Epopromycin B -- 5.18 Eupomatilone 2 -- 5.19 Fleursandols -- 5.20 (+)-Frondosin A -- 5.21 Furaquinocins -- 5.22 (+)-Heliotridine and (–)-Retronecine -- 5.23 Luminacin D -- 5.24 Mycestericin E -- 5.25 Oxyisoterihanine -- 5.26 Phaseolinic Acid -- 5.27 Pinnatoxin A -- 5.28 Salinosporamide A and its Analogues -- 5.29 Selenomilfasartan -- 5.30 Solanoeclepin A -- 5.31 Sordarin Core -- 5.32 (–)-Spinosyn A -- 5.33 (–)-Spirotryprostatin B -- 5.34 Syributins and Syringolides, Spyhydrofurans and Secosyrins -- 5.35 Tacamonine -- 5.36 Core of Eleutherobin -- 5.37 Trioxacarcinosides B -- 5.38 Tubelactomicin -- 5.39 6-Tuliposide B -- 5.40 (R)-Umbelactone. 

• Carbon-carbon bond formations and functional group transformations are the most fundamental reactions for the construction of molecular frameworks and are at the forefront of organic chemistry research. The Morita-Baylis-Hillman (MBH) type reactions possess the two most important requirements - atom economy and generation of multi-functional groups. The last decade has seen exponential growth of the MBH reaction and its applications. In fact, it is already one of the most powerful carbon-carbon bond-forming methods widely used in organic synthesis. Since the 1990s, more and more research groups have initiated work on different aspects of the MBH reaction. These have focused on the scope of the substrates, novel catalysts (especially chiral catalysts), reaction mechanisms, and synthetic applications. Consequently, there is now a need for a reference detailing the chemistry of this important reaction. This unique book summarizes the MBH reaction, aza-MBH reaction and asymmetric MBH/aza-MBH reaction including the latest research and mechanistic investigations. It provides a complete overview of MBH-type reactions aimed at synthetic organic chemists of all levels within academia and industry. The chapters cover the; origin and growth of the Morita-Baylis-Hillman reaction; reactant classes and reaction conditions; catalytic mechanisms; achiral and chiral catalytic systems; transformations of functional groups; use of Morita-Baylis-Hillman adducts and derivatives as starting materials to construct compounds with carbocyclic or heterocyclic frameworks, and the applications of the MBH reaction in synthesizing natural products.

Ämnesord

Chemical reactions  (LCSH)

Aldehydes  (LCSH)

SCIENCE / Chemistry / Organic 

Publikations- och innehållstyp

547.27 (DDC)

Uceba (kssb/8 (machine generated))