4591-65-5

Upstream product

• 5153-67-3 nitrostyrene 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 120-92-3 cyclopentanone 
• 102-96-5 (2-nitroethenyl)benzene 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 

Relevant academic research and scientific papers

A Silica-Supported Catalyst Containing 9-Amino-9-deoxy-9-epi-quinine and a Benzoic Acid Derivative for Stereoselective Batch and Flow Heterogeneous Reactions

A heterogeneous, silica-based catalyst containing 9-amino-9-deoxy-epi-quinine (or quinidine) and a derivative of benzoic acid was synthesized through radical thiol-ene click reaction. The acid component allows the in situ activation of cinchona amino group, acting as a bifunctional catalyst. The heterogenized catalysts efficiently promoted the reaction of ketones with trans-β-nitrostyrene, with diastereo- and enantioselectivity comparable to those of the homogeneous counterparts (dr up to 90:10 and 90 % ee). In addition, the catalyst retained a constant activity for at least four cycles. Finally, the supported catalyst (9-amino-9-deoxy-epi-quinine/achiral acid) was employed under continuous-flow conditions. Two enantioselective Michael reactions were in sequence performed with the same homemade packed-bed reactor. The addition of cyclohexanone to trans-β-nitrostyrene provided the evaluation of optimal residence time with high level of stereoselection (2 μL/min flow rate, 83 % ee). Furthermore, the flow reactor well performed in the preparation of warfarin (isolated yield 95 %, 78 % ee. in 16 h at room temperature). The dual (chiral amine/achiral acid) solid supported system, making an even easier work-out, represents a valuable tool for green chemistry and is attractive for large scale applications.

Interlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to β-Nitrostyrene

Fumaramide threads bearing one l-prolinamide fragment have been designed as templates for promoting the efficient formation of novel Leigh's [2]rotaxanes. Both threads and rotaxanes are shown to catalyze the asymmetric addition of ketones to β-nitrostyren

Prolinal dithioacetals: Highly efficient organocatalysts for the direct nitro-Michael additions in both organic and aqueous media

Some novel prolinal dithioacetal derivatives have been synthesized and applied as the organocatalysts for the direct Michael addition of ketones and aldehydes to nitroalkenes. High enantioselectivities and diastereoselectivities have been obtained in both

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.

Continuous asymmetric Michael addition of ketones to β-nitroolefins(1R,2R)-(+)-1,2-DPEN-modified sulfonic acid resin

A trifunctional catalyst was successfully prepared by bonding (1R,2R)-(+)-1,2-DPEN to sulfonic acid resin. The catalyst was characterized by elemental analysis, thermogravimetric (TG) analysis and infrared (IR) spectroscopy. The results indicated the coex

Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins

Based on the electrostatic adsorption between acidic resins and organocatalysts, a series of resin-supported chiral organocatalysts were designed and synthesized. They were evaluated for the asymmetric Michael addition of cyclohexanone with nitrostyrene, in which, catalyst 3 (Fig. 1) exhibited the best catalytic performance. This reaction proceeded under catalyst 3 smoothly at room temperature without any solvent or additive and could give product with high yield (95%) and good stereoselectivity (90% ee, 98:2 dr). Encouragingly, catalyst 3 was easily isolated and reused for 16 consecutive runs without obvious loss of reaction enantioselectivity. Furthermore, it was successfully applied to catalyze the reactions of a series of ketones and aldehydes with nitroolefins.

Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl L-prolinamide

A series of adamantoyl l-prolinamides have been synthesized. These compounds have been found to be highly efficient organocatalysts for the Michael addition of aldehydes and ketones to nitroalkenes. Under the optimized reaction conditions, the correspondi

Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. G

Syntheses of chiral ferrocenophanes and their application to asymmetric catalysis

N-Substituted 2-aza-[3]-ferrocenophanes were easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92% ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.

Pyrrolidine-oxyimides: New chiral catalysts for enantioselective Michael addition of ketones to nitroolefins in water

A new class of proline based organocatalysts 'pyrrolidine-oxyimides' were designed and synthesized from l-proline and hydroxyimides by employing a simple reaction protocol. These catalysts were found to be efficient in promoting asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were obtained with catalyst 1a under additive-free conditions employing water as the reaction medium.