74923-17-4Relevant academic research and scientific papers
Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required
Sharma, Sudripet,Buchbinder, Nicklas W.,Braje, Wilfried M.,Handa, Sachin
supporting information, p. 5737 - 5740 (2020/07/14)
In the micelle of PS-750-M, the presence of 3° amides from the surfactant proline linker mimics dimethylformamide, dimethylacetamide, and N-methyl-2-pyrrolidone. The resultant micellar properties enable extremely fast amide couplings mediated by 1-ethyl-3
Identification of 1,5,7-Triazabicyclododecene and Polystyrene-Supported Superbases as Efficient Hydroxylaminolysis Agents of Sterically Hindered and Epimerizable Esters
Pierre, Romain,Gaigne, Frédéric,El-Bazbouz, Ghizlane,Mouis, Grégoire,Ouvry, Gilles,Tomas, Loic,Harris, Craig S.
supporting information, p. 1102 - 1106 (2018/04/24)
In modern pharmaceutical research, the need for reliable protocols for the preparation of chemical libraries in a controlled manner is quintessential to driving the Design-Make-Test cycle in drug discovery programs. In this letter, we communicate the iden
Stereoselective Synthesis of 1,3-Diaminotruxillic Acid Derivatives: An Advantageous Combination of C-H-ortho-Palladation and On-Flow [2+2]-Photocycloaddition in Microreactors
Serrano, Elena,Juan, Alberto,Garca-Montero, Angel,Soler, Tatiana,Jimnez-Mrquez, Francisco,Cativiela, Carlos,Gomez, M. Victoria,Urriolabeitia, Esteban P.
supporting information, p. 144 - 152 (2016/01/25)
The stereoselective synthesis of ε-isomers of dimethyl esters of 1,3-diaminotruxillic acid in three steps is reported. The first step is the ortho-palladation of (Z)-2-aryl-4-aryliden-5(4H)-oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho-C-H bond of the 4-arylidene ring in carboxylic acids. The second step is the [2+2]-photocycloaddition of the C-C exocyclic bonds of the oxazolone skeleton in 2 to afford the corresponding dinuclear ortho-palladated cyclobutanes 3. This key step was performed very efficiently by using LED light sources with different wavelengths (465, 525 or 625 nm) in flow microreactors. The final step involved the depalladation of 3 by hydrogenation in methanol to afford the ε-1,3-diaminotruxillic acid derivatives as single isomers.
The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids
Cerutti, Erika,Viale, Alessandra,Nervi, Carlo,Gobetto, Roberto,Aime, Silvio
, p. 11271 - 11279 (2015/12/01)
A series of dehydroamino acids endowed with different protective groups at the amino and carboxylate moieties and with different substituents at the double bond have been reacted with parahydrogen. The observed ParaHydrogen Induced Polarization (PHIP) effects in the 1H NMR spectra are strongly dependent on the amino protecting group. DFT calculations allowed us to establish a relationship between the structures of the reaction intermediates (whose energies depend on the amido substitution) and the observed PHIP patterns.
First pre-functionalised polymeric aromatic framework from mononitrotetrakis(iodophenyl)methane and its applications
Verde-Sesto, Ester,Pintado-Sierra, Mercedes,Corma, Avelino,Maya, Eva M.,De La Campa, Jose G.,Iglesias, Marta,Sanchez, Felix
supporting information, p. 5111 - 5120 (2014/05/06)
Starting from mononitrotetrakis(iodophenyl)methane as monomer, we report the preparation of the first pre-functionalised porous aromatic frameworks (PAFs) and their application as supports for organometallic catalysts. Neutral coordinate imino-pyridine Schiff base (PAF-NPy) or chiral bis-amino (PAF-NPro) ligands were obtained by post-synthetic treatment of PAF-NH2 and treated with copper(I) or rhodium(I) to yield the corresponding supported transition-metal catalysts. The as-prepared PAF-NN-M catalysts exhibited activity and selectivity similar to that of the corresponding homogeneous catalysts and were easily removed from reaction media and recycled without loss of activity or selectivity. New copper catalysts: The preparation of pre-functionalised porous aromatic frameworks (PAFs) and their application as supports for organometallic catalysts (see figure) is reported for the first time.
The synthesis of functionalised peptides using α-lithio quinuclidine N-oxide (Li-QNO)
O'Neil, Ian A.,Bhamra, Inder
supporting information; experimental part, p. 3635 - 3638 (2009/09/30)
Deprotonation of protected peptides using lithiated quinuclidine N-oxide (Li-QNO) as a base at 0 °C, followed by addition of an alkyl halide gives C-alkylated peptide derivatives in good yield.
Amidoearbonylation of aldehydes utilizing cobalt oxide-supported gold nanoparticles as a heterogeneous catalyst
Hamasaki, Akiyuki,Liu, Xiaohao,Tokunaga, Makoto
body text, p. 1292 - 1293 (2009/12/03)
Cobalt oxide-supported gold-nanoparticles-catalyzed transformation of aldehydes and their equivalents to N-acyl-α-arnino acids was achieved. The desired products were obtained in moderate to excellent yields under milder reaction conditions than previous reports employing octacarbonyldicobalt as a catalyst. Copyright
Selective hydroalkoxycarbonylation of enamides to N-acyl amino acid esters: Synthetic applications and theoretical studies
Klaus,Neumann,Jiao,Von Wangelin, A. Jacobi,G?rdes,Strübing,Hübner,Hateley,Weckbecker,Huthmacher,Riermeier,Beller
, p. 3685 - 3700 (2007/10/03)
N-acyl amino acid esters are easily accessible from enamides by cobalt-catalyzed hydroalkoxycarbonylation in moderate to excellent yield. An important reaction parameter for selective carbonylation is the use of low hydrogen partial pressure, which prevents hydrogenation as a side reaction. The reported method is applicable to various enamides and alcohols. A DFT calculation of the catalytic cycle explains the preferred pathway of this reaction.
Solid phase reduction of oxazolones using BER-Ni2B-A simple synthesis of N-benzoylphenylalanines
Sikdar, Atul P.,Chetri, Ajoy B.,Das, Pranab J.
, p. 2878 - 2881 (2007/10/03)
Borohydride exchange resin (BER)-Ni2B is successfully used as a reagent for the solid phase reduction of the C-4 exocyclic double bond of oxazolones to give the N-benzoylphenylalanines and hence the corresponding amino acids.
