6306-53-2Relevant academic research and scientific papers
Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations
Deng, Gongtao,Jiang, Yaojia,Jiao, Yongjuan,Li, Yingmei,Wu, Jiamin,Zhang, Jinli,Zhang, Zhengyu
, p. 17462 - 17470 (2021/12/02)
A unique decarbonylation of an amino acid derivative catalytic system has been established via palladium-catalyzed C-C bond and C-N bond dual activations. By employing 8-aminoquinoline as the directing group, this transformation has been found to facilitate the high chemoselectivity to decarbonylation of amino acid derivatives rather than intramolecular deamination or cross-dehydrogenative coupling reactions. This method provides a straightforward avenue for constructing diverse functionalized amide compounds in good to excellent yields. We proposed a possible reaction pathway that may go through the C-C bond and C-N bond dual activations on the basis of the mechanistic studies.
A Novel Class of 7-Membered Heterocyclic Compounds
Bauer, Adriano,Borsos, Eszter,Maulide, Nuno
supporting information, p. 3971 - 3974 (2020/05/25)
The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully retained.
Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide-DMAD Cycloadducts
Dobesch, Matthias,Greiner, Julian,Maas, Gerhard
, p. 2987 - 3000 (2020/08/10)
Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides by a 2-carbonylphenyl moiety, are obtained.
Synthesis and study of modified polyvinyl alcohol containing amino acid moieties as anticancer agent
Samir, Ali H.,Saeed, Ruwaidah S.,Matty, Fadhel S.
, p. 286 - 294 (2018/03/21)
A series of new phthalimides compounds[3-7]a-i were synthesized from reaction of Malic anhydride, phthalic anhydride, nitro phthalic anhydride, 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, 2-(4-nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one with different amino acids as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine and Phenyl alanine [1]a-i under fusion conditions. Compounds [3-7]a-i react with SOCl2 in the presence of benzene to produce compounds [8-12]a-i. Chemical modification of Poly(vinyl alcohol)were obtained by reaction of PVA with compounds [8-12]a-i using the dimethyl formamide to give compounds [13-17]a-i. The structure of the synthesized compounds was characterized by their analytical and spectral data as, IR spectra, 1H, 13C-NMR, Elemental analysis (CHN), UV-Vis Spectroscopy, Scanning electron microscopy (SEM), Antibacterial activity were screened via two kinds of bacteria. Also, anticancer activity were examined for most of the modified polyvinyl alcohol.
Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination
Wei, Qiang,Ma, Yao,Li, Li,Liu, Qingfei,Liu, Zijie,Liu, Gang
supporting information, p. 7100 - 7103 (2018/11/24)
A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.
Cooperative Effects between Chiral Cpx–Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C?H Amidations of Phosphine Oxides
Jang, Yun-Suk,Dieckmann, Michael,Cramer, Nicolai
supporting information, p. 15088 - 15092 (2017/10/11)
An enantioselective C?H amidation of phosphine oxides by using an iridium(III) catalyst bearing an atropchiral cyclopentadienyl (Cpx) ligand is reported. A very strong cooperative effect between the chiral Cpx ligand and a phthaloyl tert-leucine enabled the transformation. Matched–mismatched cases of the different acid enantiomers are shown. The amidated P-chiral arylphosphine oxides are formed in yields of up to 95 % and with excellent enantioselectivities of up to 99:1 er. Enantiospecific reduction provides access to valuable P-chiral phosphorus(III) compounds.
Effect of different acids addition on chiral separation of phthalylvaline by quinine carbamate based chiral stationary
Fegas, Rachid,Zerkout, Said,Taberkokt, Meriem,Bettache, Zhor,Righezza, Michel
, p. 6953 - 6956 (2013/07/26)
The quinine carbamate type chiral stationary phase used for direct enantiomer separation of amino acid was studied. The influence of mobile phase composition, methanol and different acids were systematically investigated to gain an insight into the overall chiral recognition mechanism.
Hydrogen bonding chains and rings structural motifs in new series of N-phthaloyl aminocarboxylic acid derivatives. Solid state microwave synthesis, structural chemistry, computational calculations and antimicrobial activity
Al-Farhan, Khalid,Ghazzali, Mohamed,Al-Hazimi, Hassan M.A.,El-Faham, Ayman,Reedijk, Jan
scheme or table, p. 269 - 275 (2011/08/03)
A series of six N-phthaloyl aminocarboxylic acids were synthesized by using improved microwave irradiation with a multimode reactor. X-ray single crystal diffraction established the molecular structure of three N-protected aminocarboxylic acids derivatives, and spectral data agree with these in solution. The hydrogen bonding characteristics of this class of molecules are discussed on the basis of crystal structural analyses, MP2/DFT quantum calculations and Hirshfeld surfaces analyses. The relative strengths of the structural O-H?O and C-H?O hydrogen bonding chain and ring motifs are compared. Antimicrobial activities of 2-(1,3-dioxoisoindolin-2-yl)propanoic acid, 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoic acid and 2-(4-(1,3-dioxoisoindolin-2-yl)phenyl)acetic acid, were screened against three pathogenic strains; only the first two compounds were found to be quite sensitive against Gram +ve and Gram -ve bacterial strains, respectively. A relative structure-function relationship is observed.
Effect of the mobile phase acid additives on enantioselectivity of amino acid derivative using quinine carbamate based chiral stationary phase
Fegas,Bensalem,Bettache,Ouahba,Righezza
body text, p. 1582 - 1586 (2012/04/10)
Quinine carbamate-type chiral stationary phase has been used for the direct liquid chromatographic enantiomer separation of a wide range of chiral acids. In the present work, we demonstrate that this the chiral stationary phase can also be extended to chiral discrimination of amino acid derivative phthalylvalin using methanol containing different organic acids in mobile phases. The influence of mobile phase composition and enantioselectivity was systematically investigated to gain insight into the overall chiral recognition mechanism.
Catalytic asymmetric protonation of α-amino acid-derived ketene disilyl acetals using P -Spiro diaminodioxaphosphonium barfates as chiral proton
Uraguchi, Daisuke,Kinoshita, Natsuko,Ooi, Takashi
supporting information; experimental part, p. 12240 - 12242 (2010/11/19)
Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of α-amino acid-derived ketene disilyl acetals.
