1369200-70-3

Upstream product

• 3156-37-4 4-bromo-β-nitrostyrene 
• 123-38-6 propionaldehyde 
• 3156-37-4 (E)-1-bromo-4-(2-nitrovinyl)benzene 
• 3156-37-4 C₈H₆BrNO₂ 

Downstream Products

• 1431642-04-4 (2R,3S,4R)-3-(4-bromophenyl)-5,5-bis(4-(dimethylamino)phenyl)-2-methyl-4-nitropentanal 
• 1431641-97-2 C₁₁H₁₄BrNO₃ 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Synthesis of Spiro-oxindole Piperidine Derivatives That Reduce Cancer Cell Proliferation by Inhibiting MDM2-p53 Interaction

Asymmetric synthesis of pharmacologically interesting piperidine-fused spiro-oxindole derivatives has been achieved via an organocatalytic Michael/aza-Henry/hemiaminalization cascade reaction. Chiral compounds synthesized by this strategy potently inhibit

Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol

A new chiral mesoporous hybrid material was synthesized based on pyrrolidine units included in a siliceous framework, HybPyr, and integrated into the organic-inorganic structure, from a specific bis-silylated precursor. A fluoride sol-gel methodology under soft synthesis conditions and in the absence of sophisticated structural directing agents allowed the generation of a mesoporous architecture with a homogeneous distribution of active chiral moieties along the network. The hybrid material was studied by means of different characterization techniques (TGA, NMR and IR spectroscopy, chemical and elemental analyses, TEM, and textural measurements), verifying the stability and integrity of the asymmetric active sites in the solid. The hybrid material, HybPyr, is an excellent asymmetric heterogeneous and recyclable catalyst for enantioselective Michael addition of linear aldehydes to β-nitrostyrene derivatives with high stereocontrol of the reaction products.

POLYMER SUPPORTED FLUORINATED ORGANOCATALYST

Polymer supported fluorinated compound of formula I, wherein the meaning for each R1 is as disclosed in the description. These compounds are useful as catalysts, particularly in Michael addition reactions under continuous flow.

Tetrahydropyran-Based Hybrid Dipeptides as Asymmetric Catalysts for Michael Addition of Aldehydes to β-Nitrostyrenes

A new series of hybrid dipeptide-like organocatalysts based on pyranoid ?- or ζ-amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to β-nitrostyrenes. The reaction proceeds under mild conditions to afford a wide ra

Asymmetric Redox-Annulation of Cyclic Amines

Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.

Translating the Enantioselective Michael Reaction to a Continuous Flow Paradigm with an Immobilized, Fluorinated Organocatalyst

A novel polymer-supported fluorinated organocatalyst has been prepared and benchmarked in the enantioselective Michael addition of aldehydes to nitroalkenes. The system has proven to be highly efficient and displays excellent selectivities (er and dr) wit

Novel octapeptide as an asymmetric catalyst for michael reaction in aqueous media

In this work, three forms of a novel octapeptide have been evaluated as asymmetric catalysts for the Michael reaction. Low quantity catalyst loading, ecofriendly solvents, and reusability of organocatalyst successfully applied to attain excellent yields a

Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and α-aminoxy alcohols in a nonpolar medium

A proline-thiourea host-guest complex is described as a self-assembled organocatalyst for the enantioselective Michael addition of aldehydes to nitroolefins and for the asymmetric α-aminoxylation of both aldehydes and ketones. The Michael adducts were obt

Application of l-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes

The asymmetric Michael addition of aldehydes to nitroolefins was investigated using a combination of l-prolinamide derivatives and various acidic additives. (S)-1,1′-Bi-2-naphthol was found to be the most effective co-catalyst and afforded the nitroaldehy

Novel chiral ammonium ionic liquids as efficient organocatalysts for asymmetric Michael addition of aldehydes to nitroolefins

Two chiral ammonium ionic liquids 1a and 1b have been newly synthesized from commercially available (+)-cis-2-benzamidocyclohexanecarboxylic acid. These CILs have been demonstrated to be efficient organocatalysts for asymmetric Michael addition of aldehyd