131391-08-7

Upstream product

• 42953-82-2 5,5-dimethylpyrazolidin-3-one 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 141514-39-8 1-Benzyl-5,5-dimethyl-2-(methoxymethyl)-3-pyrazolidinone 
• 155281-93-9 1-benzyl-5,5-dimethyl-3-pyrazolidinone-2-carboxylic acid ethyl ester 
• 365456-25-3 1-benzyl-2-[(E)-2-butenoyl]-5,5-dimethyl-pyrazolidin-3-one 
• 657395-58-9 1-benzyl-2-[(E)-2-pentenoyl]-5,5-dimethyl-pyrazolidin-3-one 
• 657395-59-0 1-benzyl-2-[(E)-3-(ethoxycarbonyl)propenoyl]-5,5-dimethyl-pyrazolidin-3-one 
• 394220-60-1 1-benzyl-2-(3-phenyl-acryloyl)-5,5-dimethyl-pyrazolidin-3-one 
• 857636-40-9 1-benzyl-5,5-dimethyl-2-((E)-2-methylbut-2-enoyl)-pyrazolidin-3-one 
• 952198-19-5 1-benzyl-5,5-dimethyl-((E)-2-methyl-3-phenylpropenoyl)-pyrazolidin-3-one 
• 936620-87-0 1-benzyl-2-(cyclopent-1-enecarbonyl)-5,5-dimethyl-pyrazolidin-3-one 
• 936620-75-6 C₂₀H₂₆O₄N₂ 
• 936620-77-8 C₂₂H₂₄O₂N₂ 
• 936620-78-9 C₂₂H₃₀O₂N₂ 

Relevant academic research and scientific papers

An efficient synthetic methodology of chiral isoquinuclidines by the enantioselective Diels-Alder reaction of 1,2-dihydropyridines using chiral cationic palladium-phosphinooxazolidine catalyst

High purity chiral isoquinuclidines (97% ee) were obtained from the enantioselective Diels-Alder reaction of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-benzyl-2-acryloylpyrazolidin-3-one using chiral cationic palladium-phosphinooxazolidine (Pd-POZ) catalyst. The obtained DA adduct was easily converted to the chiral piperidine derivative bearing three stereogenetic centers in the structure.

Fluxional additives: A second generation control in enantioselective catalysis

The concept of "fluxional additives", additives that can adopt enantiomeric conformations depending on the chiral information in the ligand, is demonstrated in enantioselective Diels-Alder and nitrone cycloaddition reactions. The additive design is modula

The role of achiral pyrazolidinone templates in enantioselective Diels-Alder reactions: Scope, limitations, and conformational insights

We have evaluated the role of achiral pyrazolidinone templates in conjunction with chiral Lewis acids in room temperature, enantioselective Diels-Alder cycloadditions. The role of the fluxional N(1) substituent was examined, with the bulky 1-naphthylmethyl group providing enantioselectivities up to 99% ee, while templates with smaller fluxional groups gave lower selectivities. High selectivities were also observed in reactions of 7d with chiral Lewis acids derived from relatively small chiral ligands, suggesting the pyrazolidinone templates are capable of relaying stereochemical information from the ligand to the reaction center. Lewis acids capable of adapting square planar geometries, such as Cu(OTf)2, Cu(ClO4)2, and Pd(ClO4)2, were found to be particularly effective at providing high selectivities. Additionally, substitution at the C-5 position of the pyrazolidinone templates has been shown to be critical for optimal selectivity. Reactions of the optimal pyrazolidinone appended with a number of common dienophiles and various dienes demonstrate the utility of this achiral template. Furthermore, catalytic loadings could be lowered to 2.5 mol % with essentially no loss in selectivity, π-π interactions were evaluated as a means to explain the unusually high selectivity observed at room temperature. Finally, non-C2-symmetric ligands were employed as a test to determine if chiral relay was operative.

Chiral Lewis Acid Catalysis in Nitrile Oxide Cycloadditions

We describe examples of highly regio- and enantioselective nitrile oxide cycloadditions to unsaturated alkenes using substoichiometric amounts of a chiral Lewis acid. Pyrazolidinones proved to be effective achiral templates in the cycloadditions providing

Exo Selective Enantioselective Nitrone Cycloadditions

We have developed a novel method for accessing exo adducts with high enantioselectivity in nitrone cycloadditions to enoates. Pyrazolidinones proved to be effective achiral templates in the cycloadditions, providing exo adducts typically in >15:1 selectivity and 90-98% ee. The use of Lewis acids that form square planar complexes, such as copper triflate, was important for obtaining high exo selectivity. Copyright

Enantioselective conjugate addition of hydroxylamines to pyrazolidinone acrylamides

(Matrix Presented) Chiral relay templates provide amplification of selectivity in conjugate addition reactions. Reversal of stereochemistry of the product isoxazolidinones has also been demonstrated by a simple change of the Lewis acid.

Synthesis of bridged bicyclic hydrazines via endocyclic N-acylhydrazonium intermediates: A novel route to the 1-azatropane skeleton

Bicyclic molecules with the 1,7-diaza-6,6-dimethylbicyclo[2.2.1]heptane and 1,8-diaza-7,7-dimethylbicyclo[3.2.1]octane (1-aza-7,7-dimethytropane) skeleton are shown to be efficiently synthesized via cyclization reactions of endocyclic N-acylhydrazonium intermediates. By using a protected β-ketoester as the internal nucleophile, azacocaine analogues are also accessible via this methodology.

PREPARATION OF CYCLIC α-HYDRAZINO ACIDS THROUGH N-ACYLHYDRAZONIUM INTERMEDIATES

An efficient synthesis of bicyclic hydrazine derivatives (5a) and (5b) through the intermediacy of exocyclic hydrazonium ions (4a) and (4b) is described.

SYNTHESIS OF BRIDGED BICYCLIC HYDRAZINES VIA CYCLIC N-ACYLHYDRAZONIUM INTERMEDIATES

The efficient preparation of bridged diazabicyclics 1 from pyrazolidones 3 by cationic ring closure of endocyclic hydrazonium electrophiles 2 is described.