475294-87-2

Upstream product

• 5153-67-3 nitrostyrene 
• 123-38-6 propionaldehyde 
• 329969-56-4 (4-Methoxy-phenyl)-((Z)-(3S,4R)-3-methyl-5-nitro-4-phenyl-pent-1-enyl)-carbamic acid tert-butyl ester 
• 102-96-5 (2-nitroethenyl)benzene 
• 1273321-70-2 C₁₃H₁₇NO₄ 
• 590-86-3 isovaleraldehyde 
• 123-72-8 butyraldehyde 
• 1207841-27-7 C₁₃H₁₅NO₄ 
• 1273321-49-5 C₁₃H₁₅NO₄ 
• 3156-37-4 4-bromo-β-nitrostyrene 

Downstream Products

• 474924-91-9 3-methyl-4-phenyl-pyrrolidin-2-one 
• 474925-61-6 2-methyl-4-nitro-3-phenyl-butyric acid methyl ester 
• 474924-94-2 3-methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 474925-03-6 3-methyl-2-oxo-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 474925-05-8 3-allyl-3-methyl-2-oxo-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Indolinol-catalyzed asymmetric Michael reaction of aldehydes to nitroalkenes in brine

(2S,3aS,7aS)-Perhydroindolinol A facilitated the reaction of a wide range of aldehyde and nitroalkene substrates to provide Michael adducts with excellent enantioselectivities (up to 98% ee), excellent yields and high diastereoselectivities (syn/anti up t

Highly efficient and modularly tuned bicyclic organocatalyst for the enantioselective michael addition of aldehydes to nitroalkenes

A new type of bicyclic organocatalyst has been successfully applied to the asymmetric Michael addition of aldehydes to nitrostyrenes in good yields and good enantioselectivities by using a self-assembly strategy. The success of this reaction is attributed

Environmental modulation of chiral prolinamide catalysts for stereodivergent conjugate addition

Synthetic chiral catalysts generally rely on proximal functional groups or ligands for chiral induction. Enzymes often employ environmental chirality to achieve stereoselectivity. Environmentally controlled catalysis has benefits such as size and shape se

Asymmetric Organocatalysis Accelerated via Self-Assembled Minimal Structures

Self-assembling minimalistic peptides embedded with an organocatalytic moiety were designed. By controlling the formation of fibrils via external intervention, it was shown that the activation is accelerated when the organocatalyst is in its supramolecula

Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds

A chiral anthranilic pyrrolidine catalyst as a custom-made amine-catalyst was developed for the enantio- and diastereo selective Michael reaction of nitroalkenes with carbonyl compounds. In particular, a peptide-like catalyst in which an α-amino acid is a

Asymmetric Michael addition reactions of aldehydes to β-nitrostyrenes catalyzed by (S)–N-(D-prolyl-L-prolyl)-1 -triflicamido-3 -phenylpropan-2-amine

In an attempt to improve the catalytic ability of (S)–N-(D-prolyl)-1-triflicamido-3-phenylpropan-2-amine, a catalyst previously reported by us for the asymmetric Michael addition of aldehydes to β-nitrostyrenes, 4 new molecules were designed and synthesiz

Calcium carbonate as heterogeneous support for recyclable organocatalysts

The controlled synthesis of calcium carbonate particles surface-functionalized with azido groups and its subsequent copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions with organocatalysts bearing alkyne anchors allowed the preparation of novel catalytic materials. A calcium carbonate-supported α,α-diarylprolinol silyl ether prepared in this manner catalyzes Michael addition of aldehydes to trans-β-nitrostyrenes with very high diastereo- and enantioselectivity. The immobilized catalyst can be recovered by simple decantation and reused. In addition, this heterogeneous catalytic system can also be adapted to continuous-flow operation, affording a five-fold productivity increase in comparison with the batch process.

A Visible-Light-Powered Polymerization Method for the Immobilization of Enantioselective Organocatalysts into Microreactors

A versatile one-step photopolymerization approach for the immobilization of enantioselective organocatalysts is presented. Chiral organocatalyst-containing monoliths based on polystyrene divinylbenzene copolymer were generated inside channels of microfluidic chips. Exemplary performance tests were performed for the monolithic Hayashi–J?rgensen catalyst in continuous flow, which showed good results for the Michael addition of aldehydes to nitroalkenes in terms of stereoselectivity and catalyst stability with minimal consumption of reagents and solvents.

Amine Catalysis with Substrates Bearing N-Heterocyclic Moieties Enabled by Control over the Enamine Pyramidalization Direction

Stereoselective organocatalytic C?C bond formations that tolerate N-heterocycles are valuable since these moieties are common motifs in numerous chiral bioactive compounds. Such transformations are, however, challenging since N-heterocyclic moieties can i

Deactivation of Secondary Amine Catalysts via Aldol Reaction-Amine Catalysis under Solvent-Free Conditions

Despite intense interest in amine-catalyzed stereoselective reactions, high catalyst loadings of ≥10 mol % are still common and either due to low reactivity or catalyst deactivation. Yet, few deactivation pathways are well understood. Here, we unraveled the deactivation of secondary amines by undesired aldol reaction. Mechanistic studies with peptide and prolinol silyl ether catalysts showed the generality of this so-far underappreciated catalyst deactivation pathway. The insights enabled conjugate addition reactions between aldehydes and nitroolefins on a multigram scale in the absence of solvent - conditions that are attractive as environmentally benign processes - with excellent product yields and stereoselectivities in the presence of as little as 0.1 mol % of a chemoselective peptidic catalyst.