121506-76-1

Upstream product

• 874-23-7 2-acetylcyclohexanone 
• 78-94-4 methyl vinyl ketone 
• 340161-40-2 N-(2-Acetyl-1-cyclohexenyl)-L-valine diethylamide 
• 340161-42-4 N-(2-Acetyl-1-cyclohexenyl)-L-isoleucine piperidide 

Relevant academic research and scientific papers

Synthesis of spirodiones and their structure determination by X-ray crystallography

A rational synthesis of Spiro bicyclo (5,4) dec-2-ene-3-methyl-1,6-dione (1) and Spiro bicyclo (5,5) undec-2-ene-3-methyl-1,7-dione (2) from 2-acetyl cycloalkanone is described. Compounds (1) and (2) have very high potentials as important precursors to ma

Application of calcined Mg-Al hydrotalcites for Michael additions: An investigation of catalytic activity and acid-base properties

Mg-Al hydrotalcite catalysts with different Mg/Al molar ratios (0.6, 1.4, 2.2, 3.0) were calcined and tested in liquid-phase Michael additions at room temperature. The catalysts and pure oxides (MgO and Al2O 3) were characterized by

Creation of monomeric La complexes on apatite surfaces and their application as heterogeneous catalysts for Michael reactions

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.

Highly efficient C-C bond-forming reactions in aqueous media catalyzed by monomeric vanadate species in an apatite framework

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.

Michael reaction of 1,3-dicarbonyls with enones catalyzed by a hydroxyapatite-bound La complex

A hydroxyapatite-bound La complex, which functioned as an efficient heterogeneous catalyst for the Michael reaction of 1,3-dicarbonyls with enones under aqueous or solvent-free conditions, was prepared using a cation-exchange method. Further application to an asymmetric version by a fluoroapatite-bound La complex catalyst modified with (R,R)-tartaric acid is also described.

Monomeric metal aqua complexes in the interlayer space of montmorillonites as strong Lewis acid catalysts for heterogeneous carbon-carbon bond-forming reactions

Montmorillonite-enwrapped copper and scandium catalysts (Cu2-- and Sc3+-monts) were easily prepared by treating Na--mont with the aqueous solution of the copper nitrate and scandium triflate, respectively. The resulting Cu2+- and Sc3+-monts showed outstanding catalytic activities for a variety of carbon-carbon bond-forming reactions, such as the Michael reaction, the Sakurai-Hosomi allylation, and the Diels-Alder reaction, under solvent-free or aqueous conditions. The remarkable activity of the mont catalysts is attributable to the negatively charged silicate layers that are capable of stabilizing metal cations. Furthermore, these catalysts were reusable without any appreciable loss in activity and selectivity. The Cu2+-mont-catalyzed Michael reaction proceeds via a ternary complex in which both the 1,3-dicarbonyl compound and the enone are coordinated to a Lewis acid Cu2+ center.

P-BEMP: A new efficient and commercially available user-friendly and recyclable heterogeneous organocatalyst for the Michael addition of 1,3-dicarbonyl compounds

Michael addition of 1,3-dicarbonyls with various Michael acceptors has been found to be catalyzed by commercially available, user-friendly and recyclable N-phenyl-tris(dimethylamino)iminophosphorane immobilized on polystyrene resin (P-BEMP). The reaction

New auxiliaries for copper-catalyzed asymmetric Michael reactions: Generation of quaternary stereocenters at room temperature

Dialkyl amides of L-valine, L-isoleucine, and L-tert-leucine (2) are excellent chiral auxiliaries for the construction of quaternary stereocenters at ambient temperature. Enaminoesters 3, prepared from these auxiliaries 2 and Michael donors 1. undergo a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone (MVK, 4) to afford products 5 in 70-90% yield and 90-99% ee (enantiomeric excess). The exclusion of moisture or oxygen is not necessary. The auxiliaries 2 are readily available by standard procedures. After workup they can be recovered almost quantitatively.

Construction of quaternary stereocenters by nickel-catalysis of asymmetric Michael reactions

Quaternary stereocenters were constructed with an enantio-selectivity of up to 91‰ ee under aerobic conditions and at ambient temperature in the Michael reaction of β-dicarbonyl compounds and methyl vinyl ketone with Ni(OAc)2·4H2O an

A facile synthesis of 1,5-diketones from cyclic β-ketoesters under nickel-catalysis

Michael addition of cyclic β-ketoesters to α,β-unsaturated ketones has been carried out conveniently using bis(2,4-pentanedionato)nickel(II) catalyst.