1242461-29-5

Basic information

• Product Name: (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropionaldehyde
• Synonyms: (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropionaldehyde
• CAS NO: 1242461-29-5
• Molecular Weight: 245.278
• Mol File: 1242461-29-5.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropionaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropionaldehyde(1242461-29-5)
• EPA Substance Registry System: (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropionaldehyde(1242461-29-5)

Safety Data

• Hazardous Substances Data: 1242461-29-5(Hazardous Substances Data)

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 1431769-11-7 (S,E)-methyl 4-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-4-methylpent-2-enoate 
• 1431769-80-0 (S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropanoic acid 
• 1431769-22-0 (S)-tert-butyl 2-{[2-((S)-2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropanoyl]carbamoyl}-3-methylbutanoate 
• 1431769-13-9 (S)-2-(4,4-dimethyl-2-oxotetrahydrofuran-3-yl)-N-phenylacetamide 
• 1431769-12-8 (S)-methyl 2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropanoate 

Relevant articles and documents

Dendrimeric α,β-dipeptidic conjugates as organocatalysts in the asymmetric Michael addition reaction of isobutyraldehyde to N-phenylmaleimides

Abstract: A series of polyester dendrimers (1G to 3G generation) based on 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (bis-MPA) and the core of 1,3-propanediol-2-(hydroxymethyl)-2-methyl (TME) were synthesized and conjugated to the α,β-dipeptide (N

Modular Urea-Based Catalytic Platforms Bearing Flexible Pyridylmethylamine and Rigid Pyridyl-Imidazolidine Fragments

The selective and concise synthesis of new urea-based catalytic platforms is described. Each platform incorporates a urea or thiourea motif with a pyridylmethylamine or pyridyl-imidazolidine fragment. These modular catalytic platforms efficiently promote

α-Amino Acids and α,β-Dipeptides Intercalated into Hydrotalcite: Efficient Catalysts in the Asymmetric Michael Addition Reaction of Aldehydes to N-Substituted Maleimides

In this work, a series of α-amino acids (L-Phe, D-Phe, L-Trp) and several α,β-dipeptides (H2N-L-Val-N-Bn-β-Ala-COOH and H2N-L-Leu-N-Bn-β-Ala-COOH) intercalated into hydrotalcite (Mg/Al, x=0.333) were prepared by high speed ball milling (HSBM) assisted rehydration/reconstruction methods, followed by sonication and mechanical stirring. All organic-inorganic hybrid samples were characterized by powder X-ray diffraction (XRD) and FTIR-ATR spectroscopy. The catalytic activity of the resulting hydrotalcite-supported materials (natural and hybrid) was evaluated in the asymmetric Michael addition reaction of α,α-disubstituted-aldehydes to N-substituted-maleimides. Pristine (HTS), calcined (HTC) and water-reconstructed (HTR-l) hydrotalcite-derived materials exhibited very low catalytic activities, affording racemic mixtures of the anticipated Michael adduct. By contrast, hybrid materials showed better activities, especially HTR-α-amino acid catalysts afforded Michael products in up to 94 % yield and with rather high enantioselectivity (enantiomeric ratio (e.r.) up to 99 : 1) at room temperature under neat reaction conditions. The effect of solvents and Br?nsted basic or acidic additives was evaluated using the best hybrid catalyst, HTR-L-Phe. In addition, recycling and reuse of the catalyst (up to 4 cycles) and large-scale experiments was successfully carried out.

N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides

The highly asymmetric Michael addition reaction between maleimides and aliphatic aldehydes catalyzed by low-loading β-turn tetrapeptides with excellent yields and enantioselectivities at room temperature was reported. α-Branched and α-unbranched aldehydes both are suitable nucleophiles. N-Aryl, alkyl and hydrogen maleimides all are well tolerated and led to high yields and enantioselectivities. The transformation can be enlarged to the gram scale without decrease in the yield and enantioselectivity. Furthermore, the succinimides were converted into γ-lactams and γ-lactones, showing good practicality of this work. Some reaction intermediates in the proposed reaction mechanism can be captured with the HR-MS method.

1,2-Diamine-Derived (thio)Phosphoramide Organocatalysts in Asymmetric Michael Additions

Phosphoramides and thiophosphoramides were prepared from optically pure C2-symmetric 1,2-diamines and were used as chiral organocatalysts in the asymmetric Michael additions of aldehydes and ketones to N-substituted maleimides. The 1,2-diphenylethane-1,2-diamine derived thiophosphoramide, which could be prepared in good yield in a one-step procedure, was found to be more active and selective catalyst in the addition of aldehydes to various maleimide derivatives, when compared to sulfonamides having the same backbone. Products resulted in reactions of ketones with maleimides were also obtained in high yields and enantioselectivities. The thiophosphoramide derivative was also efficient in the asymmetric conjugate addition of carbonyl compounds to β-nitrostyrene and in the reaction of nitromethane with α,β-unsaturated ketones. Based on results obtained with (thio)phosphoramides in asymmetric additions to maleimides it was suggested that a weaker, more flexible hydrogen-bonding of the rigid electrophile to the catalyst is responsible for the improved performance of these bifunctional organocatalysts, as compared with sulfonamides. (Figure presented.).

The effect of chiral: N-substituents with methyl or trifluoromethyl groups on the catalytic performance of mono-and bifunctional thioureas

We evaluated thiourea organocatalysts that incorporate a chiral group which includes a trifluoromethyl moiety and contrasted their performance with non-fluorinated analogs. The comparison between such systems allows the direct study of the NH acidity of a thiourea bonded to an aliphatic substituent. In principle,-CF3 systems feature an enhanced hydrogen bond (HB) donor capacity that is undoubtedly beneficial for HB-catalysis applied to the Baylis-Hillman reaction. We found that the thiourea substituted on both nitrogens with this group accelerates this reaction like Schreiner's thiourea. On the other hand, we observed a different behavior in reactions promoted by bifunctional catalysts (thiourea-primary amine). In the Michael addition of isobutyraldehyde to methyl benzylidenepyruvate, the-CF3 containing catalysts were better than the-CH3 systems, whereas the conjugate addition to N-phenylmaleimide showed the opposite behavior. Theoretical calculations of the transition states indicated that the phenylethyl group in fluorinated and non-fluorinated compounds have different kinds of interactions with the electrophile. These interactions are responsible for a different arrangement of the electrophile and thereby the selectivity of the catalyst. Therefore, it cannot be generalized that in all cases NH acidity correlates with the performance of the catalyst, particularly, with aliphatic substituents that unlike the aromatic ones possess groups that are outside the plane of the thiourea.

Combining organocatalysis with photoorganocatalysis: photocatalytic hydroacylation of asymmetric organocatalytic Michael addition products

Organocatalysis and photoorganocatalysis are two areas of synthetic methodology that have found wide applications in organic synthesis. Herein, we report a combination of these two stategies, taking advantage of an organocatalytic Michael addition of α,α-disubstituted aldehydes to maleimides as the first step and a photocatalytic hydroacylation of diisopropyl azodicarboxylate as the second step. Employing an amino acid as the organocatalyst for the asymmetric organocatalytic part and an organic molecule as the photocatalyst, the combination of these two strategies led to the desired products. A number of alkyl- and aryl-substituted maleimides were successfully employed, while the protocol can be used on α,α-disubstituted aldehydes leading to products in moderate to high yields (44-84%) and excellent enantioselectivities (98-100% ee).

Solvent-Free Enantioselective Michael Reactions Catalyzed by a Calixarene-Based Primary Amine Thiourea

An upper-rim functionalized calix[4]arene-based thiourea installed onto the (R,R)-1,2-cyclohexanediamine scaffold was synthesized with a view to investigate its catalytic ability in enantioselective Michael additions. The reactions were found to conveniently proceed under solvent-free conditions, observing good to high enantioselectivities. From this preliminary study, the calix[4]arene unit is likely to play a role in affecting the conversion and to a lesser extent to the stereochemical outcome of the reactions through van der Waals contacts and C-H···π interactions with the substrates.

Design of Heterogeneous Organocatalyst for the Asymmetric Michael Addition of Aldehydes to Maleimides

Asymmetric Michael additions of isobutyraldehyde to maleimides catalyzed by optically pure diamines and their sulfonamides were investigated to develop heterogeneous chiral catalysts for these reactions. Encouraging results, i. e. complete transformations

Enantioselective michael addition of aldehydes to maleimides organocatalyzed by a chiral primary amine-salicylamide

A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in tolu