- Zeolite mediated Michael addition of 1,3-dicarbonyl compounds and thiols
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Zeolites, an environmentally attractive solid catalyst, proves to be an efficient catalyst for Michael addition of several 1,3-dicarbonyl compounds and thiols as donors with methyl vinyl ketone, acrolein and methyl acrylate as acceptors without any solvent are described.
- Sreekumar,Rugmini,Padmakumar, Raghavakaimal
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Read Online
- Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution
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An asymmetric synthesis of orexin receptor antagonist MK-6096 piperidine core, ((3R,6R)-6-methylpiperidin-3-yl)methanol (3), is described. The target is synthesized in four steps and 40% overall yield from methyl vinyl ketone and diethyl malonate. The key
- Chung, John Y. L.,Marcune, Benjamin,Strotman, Hallena R.,Petrova, Rositza I.,Moore, Jeffrey C.,Dormer, Peter G.
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Read Online
- Metal-dioxidoterephthalate MOFs of the MOF-74 type: Microporous basic catalysts with well-defined active sites
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The hybrid frameworks M2dobdc (dobdc4- = 2,5-dioxidoterephthalate, M2+ = Mg2+, Co2+, Ni2+, Cu2+ and Zn2+), commonly known as CPO-27 or MOF-74, are shown to be active catalysts in base-catalyzed reactions such as Knoevenagel condensations or Michael additions. Rather than utilizing N-functionalized linkers as a source of basicity, the intrinsic basicity of these materials arises from the presence of the phenolate oxygen atoms coordinated to the metal ions. The overall activity is due to a complex interplay of the basic properties of these structural phenolates and the reactant binding characteristics of the coordinatively unsaturated sites. The nature of the active site and the order of activity between the different M 2dobdc materials were rationalized via computational efforts; the most active material, both in theory and in experiment, is the Ni-containing variant. The basicity of Ni2dobdc was experimentally proven by chemisorption of pyrrole and observation by IR spectroscopy.
- Valvekens, Pieterjan,Vandichel, Matthias,Waroquier, Michel,Van Speybroeck, Veronique,De Vos, Dirk
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- Base catalytic activity of alkaline earth MOFs: A (micro)spectroscopic study of active site formation by the controlled transformation of structural anions
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A new method has been developed for generating highly dispersed base sites on metal-organic framework (MOF) lattices. The base catalytic activity of two alkaline earth MOFs, M2(BTC)(NO3)(DMF) (M = Ba or Sr, H3BTC = 1,3,5-benzenetricarboxylic acid, DMF = N,N-dimethylformamide) was studied as a function of their activation procedures. The catalytic activity in Knoevenagel condensation and Michael addition reactions was found to increase strongly with activation temperature. Physicochemical characterization using FTIR, 13C CP MAS NMR, PXRD, XPS, TGA-MS, SEM, EPR, N2physisorption and nitrate content analysis shows that during activation, up to 85% of the nitrate anions are selectively removed from the structure and replaced with other charge compensating anions such as O2-. The defect sites generated via this activation act as new strong basic sites within the catalyst structure. A fluorescence microscopic visualization of the activity convincingly proves that it is exclusively associated with the hexagonal crystals, and that reaction proceeds inside the crystal's interior. Theoretical analysis of the Ba-material shows that the basicity of the proposed Ba2+-O2--Ba2+motifs is close to that of the edge sites in BaO. This journal is
- Valvekens,Jonckheere,De Baerdemaeker,Kubarev,Vandichel,Hemelsoet,Waroquier,Van Speybroeck,Smolders,Depla,Roeffaers,De Vos
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p. 4517 - 4524
(2015/02/19)
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- Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes
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Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.
- Chandan, Nandkishor,Thompson, Amber L.,Moloney, Mark G.
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supporting information
p. 7863 - 7868
(2013/07/05)
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- An efficient synthesis of 3-alkyl-1,5,3-dioxazepanes and their use as electrophiles in double-Mannich reactions
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An efficient synthesis of 3-alkyl 1,5,3-dioxazepanes was developed for subsequent use in double-Mannich reactions with a variety of carbon-based nucleophiles. It was found that addition of methyltrichlorosilane to the dioxazepane led to a long-lasting rea
- Sparrow, Kevin,Barker, David,Brimble, Margaret A.
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experimental part
p. 1017 - 1028
(2012/02/13)
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- N-heterocyclic carbene-catalyzed michael additions of 1,3-dicarbonyl compounds
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A study of the organocatalytic activity of N-heterocyclic carbenes (NHCs) in the Michael addition of 1,3-dicarbonyl compounds has allowed us to identify 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) as an excellent catalyst for this transformatio
- Boddaert, Thomas,Coquerel, Yoann,Rodriguez, Jean
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scheme or table
p. 2266 - 2271
(2011/03/22)
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- Nickel complexes of nio-functionalized n-Heterocyclic carbenes as precatalysts for michael reactions in air at room temperature under the much preferred base-Free conditions
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A series of several new nickel precatalysts supported over N/O-functionalized N-heterocyclic carbenes (NHC) for the Michael reactions of B-dicarbonyl, B-keto ester, B-diester, and a-cyano ester compounds with a,B-unsaturated carbonyl compounds in air at ambient temperature under the much preferred base-free conditions are reported. Specifically, the nickel complexes, [1-(R1-aminocarbonylmethyl)-3-R2-imid-azol-2-ylidene]2Ni [R1 =2-C6H4(OMe); R2 = Me (1b), iPr (2b), CH2Ph (3b) and R1 = 2-CH2C4H3O; R2 =Me (4b), CH2Ph (5b)] carried out the highly convenient base-free Michael addition of the activated C-H compounds across a,B-unsaturated car- bonyl compounds in air at room temperature. The complexes 1b-5b were synthesized by the direct reaction of the respective imidazolium chloride salt with NiCl2-6H2Oin CH3CN in the presence of K2CO3 as a base. The exceptional stability of 1b-5b has been attributed to the deeply buried nickel-NHC CT-bonding molecular orbitals as evidenced from the density functional theory (DFT) studies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.
- Ray, Sriparna,Shaikh, Mobin M.,Ghosh, Prasenjit
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experimental part
p. 1932 - 1941
(2009/10/30)
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- Tin(IV) triflimidate-catalyzed cyclization of epoxy esters to functionalized δ-hydroxy-γ-lactones
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In the presence of 5 mol % of tin(IV) triflimidate, a cyclization reaction of epoxyesters to δ-hydroxy-γ-lactones proceeding in 46-98% yields without additives, ligands, or co-catalysts was observed. The cyclization to five-membered rings is greatly favor
- Antoniotti, Sylvain,Du?ach, Elisabet
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scheme or table
p. 2536 - 2539
(2009/07/26)
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- Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds
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A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, catalyzes the Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones undergo double conjugate addition with thiols producing β-keto 1,3-dithio-derivatives. In the alkylation reaction the acyclic 1,3-diketones are monoalkylated, whereas cyclic ketones undergo dialkylation under identical conditions. All these reactions were carried out without any organic solvent. The ionic liquid can also be recycled.
- Ranu, Brindaban C.,Banerjee, Subhash,Jana, Ranjan
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p. 776 - 782
(2007/10/03)
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- Promiscuous zinc-dependent acylase-mediated carbon-carbon bond formation in organic media
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A zinc-dependent acylase, d-aminoacylase from Escherichia. Coli, displays a promiscuous activity to catalyze the carbon-carbon bond formation reaction of 1,3-dicarbonyl compounds to methyl vinyl ketone in organic media. The Royal Society of Chemistry.
- Xu, Jian-Ming,Zhang, Fu,Liu, Bo-Kai,Wu, Qi,Lin, Xian-Fu
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p. 2078 - 2080
(2008/02/08)
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- Highly efficient C-C bond-forming reactions in aqueous media catalyzed by monomeric vanadate species in an apatite framework
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A calcium vanadate apatite (VAp), in which PO43- of hydroxyapatite (HAP), Ca10(PO4)6(OH) 2, is completely substituted by VO43- in the apatite framework, was synthesized. Physicochemical analysis of the VAp reveals the presence of isolated VO4 tetrahedron units with a pentavalent oxidation state. The VAp acts as a high-performance heterogeneous base catalyst for various carbon-carbon bond-forming reactions such as Michael and aldol reactions in aqueous media and the H-D exchange reactions using deuterium oxide. For example, a 200-mmol-scale Michael reaction under triphasic conditions proceeded rapidly, with an extremely high turnover number of up to 260 400 and an excellent turnover frequency of 48 s-1. No vanadium leaching was detected during the above reactions, and the catalyst was readily recycled with no loss of activity.
- Hara, Takayoshi,Kanai, Satoko,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 7455 - 7462
(2007/10/03)
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- Creation of monomeric La complexes on apatite surfaces and their application as heterogeneous catalysts for Michael reactions
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Using a cation-exchange method, an equimolar substitution of La 3+ for Ca2+ occurred by the treatment of stoichiometric hydroxyapatite (HAP: Ca10(PO4)6(OH) 2) with an aqueous solution of La(OTf)3, affording a monomeric hydroxyapatite-bound La complex (LaHAP). Physicochemical characterization by means of XRD, XPS, IR, and La K-edge XAFS analyses proved that a monomeric La3+ phosphate complex was generated on its surface. Such monomeric La3+ species function as an efficient heterogeneous catalyst for the Michael reaction of 1,3-dicarbonyls with enones under aqueous or solvent-free conditions. The work-up procedure is straightforward and the spent catalyst could be recycled without any loss of the catalytic activity. Further application to an asymmetric version was also investigated using various apatite catalysts modified with chiral organic ligands. Enantioselectivity was found to depend on the chiral ligand, solvent, and rare earth metal triflate precursor (RE(OTf)3) for the reaction of methyl 1-oxoindan-2- carboxylate with methyl vinyl ketone. Under optimized reaction conditions, a monomeric fluoroapatite-bound La complex catalyst modified with (R,R)-tartaric acid (TA-LaFAP) provided the Michael adduct quantitatively in up to 60% ee. the Royal Society of Chemistry the Centre National de la Recherche Scientifique 2006.
- Mori, Kohsuke,Oshiba, Michitaka,Hara, Takayoshi,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
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- Michael addition approach for the synthesis of novel spiro compounds and 2-substituted malonic acid derivatives from Meldrum's acid
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Novel routes for the synthesis of spiro derivatives of Meldrum's acid and 2-substituted malonic acid derivatives have been developed. Meldrum's acid was monoalkylated using a Michael addition reaction. Mono-Michael adducts were then alkylated using substituted haloalkanes, which on condensation gave spiro derivatives of Meldrum's acid. Bis Michael addition of Meldrum's acid with 1,5-diaryl-1,4-pentadien-3-one gave directly a spiro derivative of Meldrum's acid. These compounds and bis alkylated Meldrum's acid derivatives, on acidic methanolysis gave 2-substituted malonic acids.
- Chande, Madhukar S.,Khanwelkar, Rahul R.
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p. 7787 - 7792
(2007/10/03)
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- Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles
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(Chemical Equation Presented) A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles toward bis-addition to produce exclusively bis-adducts in one stroke.
- Ranu, Brindaban C.,Banerjee, Subhash
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p. 3049 - 3052
(2007/10/03)
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- Neutral Lewis bases as activators of molecular sieves in the conjugate addition of 1,3-dicarbonyl compounds
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The catalytic properties of 3 A molecular sieves in the promotion of Michael addition of 1,3-dicarbonyl compounds are significantly improved by activation with several neutral Lewis bases. Comparable efficiency can be observed under solvent-free condition
- Villano, Rosaria,Scettri, Arrigo
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p. 757 - 760
(2007/10/03)
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- Use of a solid hydrotalcite structure incorporating fluorides for basic catalysis of michael or knoevenagel reactions
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The invention concerns the use of a solid basic catalyst comprising a hydrotalcite structure wherein part at least of the compensating anions are fluoride anions F? for producing Knoevenagel of Michael condensation reactions. The invention also concerns novel solid basic catalysts comprising a hydrotalcite structure characterised by a Mg/Al molar ratio ranging between 2.5 and 3.8 wherein at least part of the compensating anions are fluoride anions F?, and methods for preparing said novel catalysts.
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Page/Page column 5-6
(2008/06/13)
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- Intramolecular heck couplings and cycloisomerizations of bromodienes and enynes with 1′,1′-disubstituted methylenecyclopropane terminators: Efficient syntheses of [3]dendralenes
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2-Bromoalka-1,n-dienes such as 9, 30 and 14 (n = 7) with tetrasubstituted methylenecyclopropane end groups, under palladium catalysis, underwent cyclization with cyclopropane-ring opening to give 2-ethenyl-3-methylene-1- cycloalkenes 41 (n = 6), 42 (n = 7
- Braese, Stefan,Wertal, Hanno,Frank, Daniel,Vidovic, Denis,De Meijere, Armin
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p. 4167 - 4178
(2007/10/03)
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- Highly efficient 1,4-addition of 1,3-diesters to conjugated enones by In/TMSCl
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Organoindium reagents derived from indium and diethyl bromomalonates were added to a wide range of conjugated enones in a 1,4-fashion in the presence of TMSCl under mild conditions, and corresponding oxo-1,3-diesters were obtained in good to excellent yields.
- Lee, Phil Ho,Seomoon, Dong,Lee, Kooyeon,Heo, Yunkiu
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p. 2510 - 2513
(2007/10/03)
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- Catalytic C-C bond formation promoted by Mg-Al-O-t-Bu hydrotalcite
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Mg-Al-O-t-Bu-hydrotalcite catalyst was found to be an efficient, environmentally attractive and selective solid base catalyst for 1,4 Michael addition. Mg-Al-O-t-Bu hydrotalcite is also effective for simple synthesis of α,β-unsaturated esters and nitriles by condensation of the corresponding activated carboxylic esters or nitriles with various aldehydes by Knoevenagel condensation. These reactions proceeded at room temperature at a greater rate in the presence of Mg-Al-O-t-Bu hydrotalcite than in the presence of any of the other catalysts examined. (C) 2000 Elsevier Science Ltd.
- Choudary,Lakshmi Kantam,Kavita,Venkat Reddy,Figueras
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p. 9357 - 9364
(2007/10/03)
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- Michael additions of carbonucleophiles to butenone catalyzed by the non- hydride [Ru(O2CH)(CO)2(PPH3)]2 complex
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[Ru(μ-O2CH)(CO)2(PPh3)]2 in acetonitrile is an efficient catalyst precursor for the Michael addition of soft carbonucleophiles to butenone. The utilization of terminal alkynes as donors makes possible the selective formation of γ,δ-ynones.
- Picquet,Bruneau,Dixneuf
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p. 3937 - 3948
(2007/10/03)
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- MCM-41-Quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts
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Quaternary organic tetraalkylammonium hydroxide grafted on MCM-41 is a strong Bronsted base catalyst, and represents a useful alternative to soluble bases in reactions such as Knoevenagel condensations, Michael additions and aldol condensations because of their high catalytic activity under mild conditions, and good stability.
- Rodriguez, Isabel,Iborra, Sara,Corma, Avelino,Rey, Fernando,Jorda, Jose L.
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p. 593 - 594
(2007/10/03)
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- Cerium catalyzed michael addition of 1,3-dicarbonyl compounds under microwave irradiation
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Cerium chloride heptahydrate proves to be an efficient catalyst for Michael addition of 1,3-dicarbonyl compounds, through a simple solvent free reaction under microwave irradiations.
- Boruah, Anima,Baruah, Mukulesh,Prajapati, Dipak,Sandhu, Jagir S.
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p. 653 - 658
(2007/10/03)
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- TITANIUM CATALYST, ORGANOTITANIUM REACTION REAGENT, PROCESSES FOR PRODUCING THESE, AND METHOD OF REACTION USING THESE
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A titanium catalyst for reaction between a carbon-carbon unsaturated bond and a compound having an electrophilic functional group or an electrophilic reagent, said titanium catalyst being composed of a titanium compound represented by the formula (1) below TiX1X2X3X4(where X1, X2, X3, and X4denote independently a halogen atom, C1-20alkoxyl group, aralkyloxy group, aryloxy group, or -NRxRy group (where Rx and Ry denote independently a C1-20alkyl group or aralkyl group), and any two of X1, X2, X3, and X4may form a ring.) and a Grignard reagent represented by the formula (2) below in a molar amount 1.5-2.5 times as much as the titanium compound. R1MgX5(where R1denotes a C2-10alkyl group having a hydrogen atom at the β position and X5denotes a halogen atom.) The titanium catalyst of the present invention activates the carbon-carbon unsaturated bond, which has a comparatively low reactivity, thereby catalyzing the reaction with an electrophilic functional group. It is inexpensive and industrially advantageous. When applied to reaction between a carbon-carbon unsaturated bond and an electrophilic functional group, it yields industrially a variety of adducts of a compound having a carbon-carbon unsaturated bond and a compound having an electrophilic functional group, and it also yields a variety of intramolecular adducts of a compound having a carbon-carbon unsaturated bond and an electrophilic functional group in the same molecule.
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- BiCl3 or Cdl2 catalyzed Michael addition of 1,3-dicarbonyl compounds under microwave irradiations
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Cdl2 proves to be an efficient catalyst for Michael addition of 1,3-dicarbonyl compounds under microwave irradiations, through a simple solvent free reaction.
- Baruah, Bipul,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
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p. 1449 - 1450
(2007/10/03)
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- A new method for the preparation of Michael adducts and cyclic enones using lithium chloride-hexamethylphosphoramide system
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A new procedure using lithium chloride in hexamethylphosphoramide was found to be useful for the synthesis of Michael-type adducts and cyclic enones. Selectivity for the two products could be controlled by altering the reaction temperature employed. The urea-type solvents were also examined instead of hexamethylphosphoramide.
- Ozaki,Kubo,Okamura,Kim
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p. 734 - 737
(2007/10/02)
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- LITHIUM HYDROXIDE-CATALYZED CONJUGATE ADDITION OF β-DICARBONYL COMPOUNDS
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Lithium hydroxide proves to be a very efficient catalyst for Michael addition of β-dicarbonyl compounds 1.The application of the methodology to α,γ-diketo esters and α-keto γ-diesters 4 allows an easy approach to δ-diketones and δ-keto esters 5, respectiv
- Bonadies, Francesco,Forcellese, Maria Luigia,Locati, Ludovica,Scettri, Arrigo,Scolamiero, Cristina
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p. 467 - 468
(2007/10/02)
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- Cyclization reactions leading to β-hydroxyketo esters
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The purpose of the research was to synthesize β-diketo esters and to evaluate them for anticonvulsant activity. The reaction of methyl vinyl ketone with dimethyl malonate in the presence of potassium carbonate gave an uncyclized product that underwent a Claisen condensation to yield methyl 2- hydroxy-4-oxocyclohex-2-en-1-oate (5a). Similarly, other cyclized β- hydroxyketo esters were prepared, and their spectrometric data confirmed that the enol tautomers were preferred to the β-diketo tautomers. The synthetic work clarified the reaction pathway for the Michael addition of malonate esters to enones. Of the intermediates and products tested for anticonvulsant activity, dimethyl 2,2-bis-(3-oxobutyl)malonate (9a) was found to possess anticonvulsant property. However, it is emphasized that the β-hydroxyketo esters could be useful intermediates in the synthesis of enaminone anticonvulsants.
- Nicholson,Edafiogho,Moore,Farrar,Scott
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- Surface-Mediated Phase Reaction: Dramatic Improvement of Michael Reaction on the Surface of Alumina
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The Michael reaction of several 1,3-dicarbonyl compounds, nitroalkanes, and thiols as donors with methl vinyl ketone, acrolein, methyl acrylate, methyl methacrylate, and mesityl oxide as acceptors on the surface of alumina without any solvent proceed very efficiently and furnish high yield of adducts. Key Words: Michael reaction; Al2O3; dramatic improvement
- Ranu, Brindaban C.,Bhar, Sanjay
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p. 1327 - 1332
(2007/10/02)
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- THE MICHAEL ADDITION IN MICELLAR PHASE
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Butenone, 1, and 3-penten-2-one, 2, underwent conjugated addition (Michael reaction) when treated with a β-dicarbonyl compound (2,4-pentanedione, ethyl 3-oxobutanoate, ethyl propanedioate) in aqueous solution, in the presence of a cationic surfactant.The yield of the reaction depended on a number of factors (temperature, concentration, nucleophile precursor, surfactant and structure of the α,β-unsaturated substrate).
- Bassetti, Mauro,Cerichelli, Giorgio,Floris, Barbara
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p. 527 - 532
(2007/10/02)
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- LITHIUM IODIDE-CATALYZED CONJUGATE ADDITION OF β-DICARBONYL COMPOUNDS
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Lithium iodide proves to be a very efficient catalyst for Michael addition of β-dicarbonyl compounds.The successful application of this methodology to α,β-unsaturated aldehydes allows an improved approach to 5,6-disubstituted cyclohex-2-en-1-ones.
- Antonioletti, R.,Bonadies, F.,Monteagudo, E. S.,Scettri, A.
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p. 5373 - 5374
(2007/10/02)
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- Surface-mediated solid phase michael reaction: Dramatic acceleration on alumina
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The Michael reaction of several β-dicarbonyl compounds, ethyl cyanoacetate, and diethyl malonate as donors with methyl vinyl ketone, acrolein and methyl acrylate as acceptors are carried out very efficiently on Al2O3 surface without any solvent.
- Ranu, Brindaban C.,Bhar, Sanjay,Sarkar, Dipak C.
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p. 2811 - 2812
(2007/10/02)
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- REACTIONS OF TITANIUM DERIVATIVES OF CERTAIN CH ACIDS WITH CARBONYL COMPOUNDS. I. CROTONIC CONDENSATIONS WITH THE TITANIUM DERIVATIVES OF MALONIC ESTER, CYANOACETIC ESTER, AND MALONONITRILE
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The titanium derivatives of malonic ester, cyanoacetic ester, and malononitrile obtained by the reaction of the corresponding sodium salts with (i-PrO)3TiCl, react with aldehydes in THF at -78 to 20 deg C, forming the products from crotonic condensation.If α,β-unsaturated aliphatic α-bromo and keto aldehydes are used, the yields of the corresponding alkylidenemalonic and alkylidenecyanoacetic esters are substantially higher than under the conditions of the Knoevenagel reaction.
- Kasatkin, A. N.,Biktimirov, R. Kh.,Tolstikov, G. A.,Khalilov, L. M.
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p. 1029 - 1037
(2007/10/02)
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- CATALYSIS OF THE MICHAEL REACTION
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Two nearly equivalent procedures have been evolved for catalysis of the Michael reaction: (i) potassium t-butoxide deposited on xonotlite; and (ii) aluminasupported potassium fluoride.These catalysts will undergo 150+ turnovers and enable Michael additions to be run at room temperature or below in good yields.
- Laszlo, Pierre,Pennetreau, Pascal
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p. 2645 - 2648
(2007/10/02)
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- COPPER(II) IN ORGANIC SYNTHESIS. I. COPPER(II) ACETATE AS CATALYST FOR MICHAEL REACTION UNDER NEUTRAL CONDITIONS
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Commercial copper(II) acetate monohydrate is found to be a useful catalyst for the Michael reaction.The neutral conditions avoid side reactions, increase yields and allow a simpler separation of the adducts.A mechanism of action is proposed for the catalyst and a comparison with previously proposed "neutral" methods is discussed.
- Coda, Andreina Corsico,Desimoni, Giovanni,Righetti, Pierpaolo,Tacconi, Gianfranco
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p. 417 - 420
(2007/10/02)
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- Nickel-Catalyzed Michael Additions of β-Dicarbonyls
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Bis(2,4-pentanedionato)nickel(II) is found to be a mild, efficient, and simple to use catalyst for the Michael additions of β-dicarbonyls.Yields are higher than with traditional strongly basic catalysts, unwanted side reactions are reduced, and workup procedures are greatly simplified.The reactions appear to be quite general as β-diketones, β-keto esters, β-keto amides, and β-diesters are all found to react.A rational mechanism which suggests further research is presented.
- Nelson, John H.,Howells, Peter N.,DeLullo, George C.,Landen, George L.,Henry, Ronald A.
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p. 1246 - 1249
(2007/10/02)
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