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Upstream product

• 699-18-3 2-[(E)-2-nitroethenyl]furan 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-94-1 cyclohexanone 
• 699-18-3 2-(2-nitrovinyl)furan 
• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 

Relevant academic research and scientific papers

Asymmetric Michael reaction promoted by chiral thiazolidine-thiourea catalyst

In this work, we report the synthesis and characterization of three new thiazolidine- and thiourea-based chiral organocatalysts. These compounds were successfully applied in asymmetric Michael addition reactions between different ketones and nitrostyrenes leading to products in up to 85% yield, >96:4 r.d. and 97% e.e. Computational studies were used to better visualize the proposed transition state and explain the observed stereoselectivities. One of the new catalysts was also successfully applied in an aldol addition between cyclohexanone an p-nitrobenzaldehyde leading to product in 80% yield, >96:4 d.r. and 80% e.e.

Remarkable Effect of tert-Amine Additives in the Asymmetric Direct Michael Reaction of Ketones with β-Arylnitroethenes Catalyzed by an L-Hydroxyproline-Based Amino Tf-Amide Organocatalyst

A catalytic asymmetric direct Michael reaction of ketones with trans-β-arylnitroethenes can be achieved under the influence of optically pure L-hydroxyproline-based secondary-amino aromatic Tf-amide organocatalyst. The effect of the trialkylamine base additive such as diethylmethylamine is of paramount importance to accomplish high reactivity and enantioselectivity in this asymmetric Michael reaction.

Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes

Abstract: Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes

Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts

Novel bifunctional pyrrolidine-based organocatalysts for the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optim

Asymmetric conjugate additions of carbonyl compounds to nitroalkenes under solvent-free conditions using fluorous diaminomethylenemalononitrile organocatalyst

The novel fluorous organocatalyst bearing a diaminomethylenemalononitrile motif is prepared. The fluorous organocatalyst efficiently promotes asymmetric conjugate additions of ketones to nitroalkenes and results in high yields of these addition products with excellent enantioselectivities under solvent-free conditions.

Asymmetric conjugate additions of carbonyl compounds to nitroalkenes under solvent-free conditions using fluorous diaminomethylenemalononitrile organocatalyst

The novel fluorous organocatalyst bearing a diaminomethylenemalononitrile motif is prepared. The fluorous organocatalyst efficiently promotes asymmetric conjugate additions of ketones to nitroalkenes and results in high yields of these addition products w

An ionic liquid containing L-proline moiety as highly efficient and recyclable chiral organocatalyst for Michael addition

A novel chiral ionic liquid containing proline moiety was synthesized. It can be used as a highly efficient and recyclable chiral organocatalyst for Michael addition of cyclohexanone with (E)-β-nitroalkenes in methanol at room temperature. The Michael add

Pyrrolidine modified PANF catalyst for asymmetric Michael addition of ketones to nitrostyrenes in aqueous phase

Three chiral pyrrolidine functionalized polyacrylonitrile fiber catalysts have been designed, prepared, and evaluated for their catalytic performance in asymmetric Michael addition of ketones to nitrostyrenes in water. With the optimized catalysts and conditions in hand, their reaction scope for nitrostyrenes was explored. Then the fiber catalysts were further applied to a packed-bed reactor for continuous-flow Michael addition. Based on the fact that organic solvent can inhibit the catalytic activity, a novel microenvironment catalytic mechanism is proposed.

Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis

A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol?1 of energy towards the product formation.

4-Fluoro and 4-hydroxy pyrrolidine-thioxotetrahydropyrimidinones: Organocatalysts for green asymmetric transformations in brine

The synthesis of both trans- and cis-diastereomers of pyrrolidinine-thioxotetrahydropyrimidinone bearing either a fluorine or a hydroxyl group was accomplished. The new compounds were tested for their catalytic properties in a variety of asymmetric organic transformations and compared with the first generation catalyst. It was found that the new catalysts could efficiently catalyze the reactions in brine, without the use of organic solvent, and by employing an almost stoichiometric amount of reagents. Thus, the products were isolated by simple extractions, avoiding the use of chromatography in excellent yields, diastereoselectivities, and enantioselectivities.