1574-87-4

Upstream product

• 75-52-5 nitromethane 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 943-88-4 4-(p-methoxyphenyl)-3-butene-2-one 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 67-64-1 acetone 
• 123-11-5 4-methoxy-benzaldehyde 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 

Downstream Products

• 91563-34-7 4-(4-methoxy-phenyl)-2-methyl-pyrrolidine 

Relevant academic research and scientific papers

Stereodivergent Evolution of Artificial Enzymes for the Michael Reaction

Enzymes are valuable biocatalysts for asymmetric synthesis due to their exacting stereocontrol. Changing the selectivity of an existing catalyst for new applications is, however, challenging. Here we show that, in contrast, the stereoselectivity of an art

Concentration Effect in the Asymmetric Michael Addition of Acetone to β-Nitrostyrenes Catalyzed by Primary Amine Thioureas

Bifunctional primary amine thiourea (PAT) organocatalysts show remarkable improvement in enantioselectivity and catalytic activity (turnover frequency) in the asymmetric Michael addition of acetone to β-nitrostyrenes upon dilution. Mechanistic investigati

Enantiocomplementary synthesis of γ-nitroketones using designed and evolved carboligases

Artificial enzymes created by computational design and directed evolution are versatile biocatalysts whose promiscuous activities represent potentially attractive starting points for divergent evolution in the laboratory. The artificial aldolase RA9S.5-8, for example, exploits amine catalysis to promote mechanistically diverse carboligations. Here we report that RA95.5-8 variants catalyze the asymmetric synthesis of γ-nitroketones via two alternative enantiocomplementary Michael-type reactions: enamine-mediated addition of acetone to nitrostyrenes, and nitroalkane addition to conjugated ketones activated as iminium ions. In addition, a cascade of three aldolasecatalyzed reactions enables one-pot assembly of γ-nitroketones from three simpler building blocks. Together, our results highlight the chemical versatility of artificial aldolases for the practical synthesis of important chiral synthons.

(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.

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

Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed i

Lipase/acetamide-catalyzed carbon-carbon bond formations: A mechanistic view

A lipase B from Candida antarctica (CALB)/acetamide-catalyzed Michael addition of less-activated ketones and aromatic nitroolefins has been developed, which is particularly interesting because neither CALB nor acetamide can independently catalyze the reaction to any appreciable extent. This co-catalyst system was applicable to the Michael additions of cyclic and acyclic ketones to a series of aromatic and heteroaromatic nitroolefins. Hydrogen bonds between acetamide and cyclohexanone were confirmed for the observed activation by experimental facts, and new mechanistic insights into CALB/acetamide co-catalysis are presented. Copyright

Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN)

The highly enantioselective addition of acetone to 2-nitrostyrene, using N-diphenylphosphinyl-trans-1,2-diphenylethane-1,2-diamine (PODPEN) as a catalyst, is described.

C3-symmetric proline-functionalized organocatalysts: Enantioselective michael addition reactions

C3-Symmetric, tripodal catalyst 4 based on 1,3,5- triethylbenzene, which incorporates the features of a molecular receptor, is shown to catalyze Michael addition reactions ofcarbonyl compounds to β-nitrostyrenes in a high stereoselectivity (up to 99:1a dr and up to 98%ee). Copyright

Simple Cyclohexanediamine-Derived Primary Amine Thiourea Catalyzed Highly Enantioselective Conjugate Addition of Nitroalkanes to Enones

A highly enantioselective conjugate addition of nitroalkanes to enones has been developed. The process Is efficiently catalyzed by a simple chiral cyclohexanediamine-derived primary amine thiourea with a broad substrate scope.