50899-67-7

Upstream product

• 67-56-1 methanol 
• 25616-13-1 alanine hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 75984-42-8 methyl N-p-methoxybenzylidene-2-(2'-cyanoethyl)alaninate 
• 75984-47-3 dimethyl N-methoxybenzylidene-2-methylglutamate 
• 1169983-84-9 (1R,3S,3aR,6aS)-methyl octahydro-3-(4-methoxyphenyl)-1,5-dimethyl-4,6-dioxopyrrolo[3,4-c]pyrrole-1-carboxylate 
• 1370441-36-3 C₂₉H₃₁FN₂O₇ 
• 1370441-40-9 C₃₄H₃₃BrN₂O₇ 
• 1370441-26-1 C₃₀H₃₄N₂O₈ 
• 28385-45-7 L-α-methylphenylalanine methyl ester 
• 38574-55-9 (R)-(-)-methyl 2-amino-2-methyl-3-phenylpropionate 
• 1610827-58-1 C₂₇H₃₉NO₆ 
• 1610827-59-2 C₂₇H₃₉NO₆ 
• 1610827-75-2 C₂₇H₃₉NO₆ 
• 1610827-76-3 C₂₇H₃₉NO₆ 
• 209627-18-9 2-(4-methoxybenzylamino)propionic acid methyl ester 
• 872984-87-7 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-propionic acid methyl ester 

Relevant academic research and scientific papers

Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies

The discovery of efficient organocatalysts is generally carried out by thorough experimental screening of different candidates. We recently reported an efficient organocatalyst for iminium-ion-based asymmetric Diels-Alder reactions following a rational design approach. This result encouraged us to test this optimal catalyst in the mechanistically related Friedel-Crafts alkylation of indoles, but to our surprise, almost null enantioselectivity was observed. The results did not significantly improve with structurally related catalysts, and a totally unexpected facial selectivity inversion was also noticed. Using DFT calculations by modeling the competing transition structures with ONIOM, we could unravel the origins of those findings, further employed to predict the most efficient catalyst for this new transformation. The computational results were validated experimentally (up to 92:8 er), providing another successful example of a general strategy to accelerate catalyst development which still remains underexplored.

Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while

Synthesis of novel multi-functionalized pyrrolidines by [3 + 2] dipolar cycloaddition of azomethine ylides and vinyl ketones

Abstract: An efficient and easy synthetic route to substituted pyrrolidine derivatives has been established through [3 + 2] dipolar cycloaddition of vinyl ketones and azomethine ylides. The reactions proceed smoothly, under mild conditions, affording mode

Ag2CO3/CA-AA-amidphos multifunctional catalysis in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides

The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up to 96% ee).

Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones

Enantiomerically pure pyrrolidines have been obtained by 1,3-dipolar cycloaddition of stabilized azomethine ylides and sugar enones (dihydropyranones) derived from pentoses. Thus, the S-enone (menthyl 3,4-dideoxy-(1S)-pent-3-enopyranosid-2-ulose) was prepared from d-xylose, while the R analogue was obtained from l-arabinose. The dipoles were generated in situ from α-arylimino esters of common amino acids (glycine, alanine, or phenylalanine) and aromatic aldehydes (benzaldehyde, 3-formylpyridine and 4-methoxybenzaldehyde). Under optimized conditions, the cycloaddition reactions were highly diastereo- and regioselective to yield, in most of the cases, a very major adduct of the 16 theoretically possible. The diastereoselectivity relies on the strict stereocontrol exerted by the stereogenic center of the pyranone. Thus, the (S)-enone, derived from d-xylose, gave tetrasubstituted pyrrolidines having a defined stereochemistry for the four stereocenters of the ring, while they had the opposite configuration when starting from the (R)-dihydropyranone. Furthermore, some endo-cycloadducts underwent isomerization of the carbons vicinal to the nitrogen atom to afford pyrrolidines with a rather unusual stereochemistry for the direct dipolar cycloadditions.

Highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides catalyzed by AgOAc/TF-BiphamPhos

A novel and highly efficient AgOAc/TF-BiphamPhos catalytic system shows excellent reactivity, diastereo-/enantioselectivity and structural scope in asymmetric 1,3-dipolar cycloaddition of azomethine ylides, especially derived from various α-substituted α-amino acids, with N-substituted maleimides and other electron-deficient alkenes.

Azetidine-derived amino acids versus proline derivatives. Alternative trends in reverse turn induction

(Figure Presented) The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides R2CO-2-R1Aze-L- Ala-NHMe has been analyzed by molecular modeling, 1H NMR, and FT-IR studies. The conformation

Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-wittig reactions

Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.

"Nitrono" Peptides, I. - An Isomeric and Isoelectronic Equivalent of the Peptide Bond

Optically active Boc-α-L-amino aldehydes 1 are converted with N-hydroxy-α-L-amino acid methyl esters 2 into the N-blocked "nitrono" dipeptide esters 3a-l.

X=Y-ZH Systems as Potential 1,3-Dipoles. Part 1. Background and Scope

X=Y-ZH Systems are considered in general terms and divided into four classes according to the number of constituent atoms that possess lone-pair electrons.Those systems in which the central Y atom possesses a lone pair are shown to be capable of participa