76292-76-7

Upstream product

• 6829-40-9 aminomalonic acid diethyl ester 
• 100-52-7 benzaldehyde 
• 13433-00-6 diethyl aminomalonate hydrochloride 

Downstream Products

• 1092380-07-8 diethyl-4-nitro-3,5-diphenylpyrrolidine-2,2-dicarboxylate 

Relevant academic research and scientific papers

A simple synthesis of polysubstituted pyrrolidines by an organocatalytic three-component approach featuring a one-pot condensation and [3+2]-cycloaddition reaction in aqueous medium

A simple one-pot procedure was developed for [3+2]-cycloaddition reactions of α,β-unsaturated aldehydes, diethyl aminomalonate, and aromatic aldehydes in the presence of diphenyl[(2S)-pyrrolidin-2-yl]methanol as catalyst. This reaction converts simple, co

One-pot, three-component, highly diastereoselective metal-free synthesis of 2,3,4,5-tetrasubstituted pyrrolidines

An extremely efficient, highly diastereoselective, metal-free synthesis of 2,3,4,5-tetrasubstituted pyrrolidines is described. The three-component reaction between aldehydes, aminomalonates, and nitroalkenes proceeds with high diastereoselectivities and h

Sequential Ir-Catalyzed Allylation/2-aza-Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines?

Sequential Ir-catalyzed asymmetric allylation/2-aza-Cope rearrangement of arylidene aminomalonates with allylic carbonates was successfully developed, and a variety of enantioenriched homoallylic amine derivatives were obtained in high yields with good chirality transfer and excellent E/Z-geometry control (up to 99% yield, 96% ee). Compared with previous dual catalytic system established for this transformation, the current mono metal catalytic system provides a simpler and more practical protocol employing the readily available starting materials.

Axially Chiral Cyclic Phosphoric Acid Enabled Enantioselective Sequential Additions

Efficient axially chiral cyclic phosphoric acid catalyzed enantioselective sequential additions of 2-aryl-3H-indol-3-ones, aldehydes, and diethyl 2-aminomalonate have been developed, and a new type of nitrogen-containing heterocyclic compounds, 2,3-dihydro-1H-imidazo[1,5-a]indol-9(9aH)-one derivatives, were prepared in good yields and excellent ee values with a wide functional group tolerance, in which the reactivity and enantioselectivity of the substrates were enabled by our newly developed axially chiral cyclic phosphoric acid, (R)-CYC-9-CPA. Furthermore, the corresponding 1H-imidazo[1,5-a]indol-9(9aH)-ones were constructed through the easy oxidation of 2,3-dihydro-1H-imidazo[1,5-a]indol-9(9aH)-one derivatives.

Substitution of the Dimethylamino Group in Gramines and One-Pot Cyclization to Tetrahydro-β-carbolines Using a Triazine-Based Activating Agent

A new method for the substitution of 3-[(dimethylamino)methyl]indoles (gramines) with malonate-based nucleophiles was developed using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) as the activating agent for the dimethylamino group. The reaction was completed in 1.5-6 h at room temperature in the presence of a tert-amine base and lithium salt. CDMT afforded superior results to methyl iodide, a common activating agent for the dimethylamino group in Mannich bases, particularly in the reactions of 1-substituted gramines. The reactivity of the possible intermediates, bis(indol-3-ylmethyl)dimethylammonium salts, was examined to obtain mechanistic insights on the reaction. This substitution method with CDMT enabled the sequential transformation of gramines: substitution with (N-alkylidene)aminomalonates followed by the Pictet-Spengler reaction under acidic conditions afforded 1,2,3,4-tetrahydro-β-carboline derivatives in one pot.

Catalytic chemoselective [3+3] cycloadditions of azomethine ylides with quinone monoimides leading to the construction of a dihydrobenzoxazine scaffold

A chemoselective [3+3] cycloaddition of in situ generated azomethine ylides with quinone monoimides has been established, which efficiently led to the construction of dihydrobenzoxazine frameworks with biological relevance, with excellent chemoselectiviti

An amine-catalyzed enantioselective [3+2] cycloaddition of azomethine ylides and α,β-unsaturated aldehydes: Applications and mechanistic implications

The catalytic enantioselective [3+2] cycloaddition between azomethine ylides and α,β-unsaturated aldehydes catalyzed by α,α-diphenylprolinol has been studied in detail. In particular, the reaction has been extended to the use of 2-alkenylidene aminomalonates generated in situ as azomethine ylide precursors. These reactions lead to the formation of pyrrolidines containing a 5-alkenyl side chain with potential for chemical manipulation. Moreover, a detailed and concise computational study has been carried out to understand the exact nature of the mechanism of this reaction and especially the consequences derived from the incorporation of the chiral secondary amine catalyst on the reaction pathway.

Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines

Isoindoline derivatives with high enantiomeric purity (up to 98% ee) have been accessed by formal double arylation of azomethines.

Reaction control in the organocatalytic asymmetric one-pot, three-component reaction of aldehydes, diethyl α-aminomalonate and nitroalkenes: Toward diversity-oriented synthesis

A study was conducted to demonstrate diversity-oriented synthesis and reaction control in the organocatalytic asymmetric one-pot and three-component reaction of aldehydes, diethyl α-aminomalonate, and nitroalkenes. The study investigated the reaction of α-imino acetate and nitrostyrene, catalyzed by thiourea-tertiary amine in toluene at ambient temperature. It was found that the introduction of another ethoxycarbonyl group at the α-position of α-imino acetate will facilitate the generation of the azomethine ylide intermediate through tertiary amine activation. A variety of nitroalkene and aldehyde substrates were investigated, to establish the general utility of the catalytic transformation, after finding the favorable reaction conditions. A range of catalysts, bearing an active thiourea moiety were also screened through one-pot, three-component reaction of benzaldehyde, to investigate the predictions.