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Upstream product

• 5153-67-3 nitrostyrene 
• 120-92-3 cyclopentanone 
• 102-96-5 (2-nitroethenyl)benzene 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Novel C2-symmetric phenylglycine derivatives as organocatalysts of the Michael reaction between nitroalkenes and ketones

A comprehensive study of the activity of the amide-type organocatalysts based on (R)- and (S)-phenylglycine and 1,2-di(2-pyridyl)-1,2-diaminoethane in the asymmetric Michael reaction between various nitroalkenes and ketones was carried out. The products o

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.

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

L -Prolinal Dithioacetal: A Highly Effective Organocatalyst for the Direct Nitro-Michael Addition to Selected Cyclic and Aromatic Ketones

The synthesis of novel l -prolinal dithioacetal and its application as an organocatalyst for the direct Michael addition of cyclic ketones and acetophenone derivatives to trans -β-nitrostyrene and related compounds is described. The prolinal dithioacetal

Concerted catalysis by nanocellulose and proline in organocatalytic Michael additions

Cellulose nanofibers (CNFs) have recently attracted much attention as catalysts in various reactions. Organocatalysts have emerged as sustainable alternatives to metal-based catalysts in green organic synthesis, with concerted systems containing CNFs that are expected to provide next-generation catalysis. Herein, for the first time, we report that a representative organocatalyst comprising an unexpected combination of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-oxidized CNFs and proline shows significantly enhanced catalytic activity in an asymmetric Michael addition.

Pyrrolidine-carbamate based new and efficient chiral organocatalyst for asymmetric Michael addition of ketones to nitroolefins

The novel ((S)-pyrrolidin-2-yl)methyl phenylcarbamate was synthesized and used as an efficient organocatalyst for the asymmetric Michael addition of cyclic/acyclic ketones to nitroolefins. Interestingly, the resulting Michael adducts were obtained in good to high yields (up to 96%) with excellent stereoselectivity (ee up to >99%, dr up to >99:1) without using any additive.

The carbamate esters as organocatalysts in asymmetric Michael addition reactions in aqueous media: When pyrrolidine backbone surpasses 1,2- diaminocyclohexane

A pyrrolidine ring containing carbamate ester, pyrrolidine-2-ylmethyl-carbamic acid isobutyl ester has been synthesized. The newly developed pyrrolidine ring containing carbamate ester surpassed 1,2- diaminocyclohexane derived carbamate ester in asymmetri

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.