74273-47-5Relevant articles and documents
Catalytic Aerobic Cross-Dehydrogenative Coupling of Azlactones en Route to α,α-Disubstituted α-Amino Acids
Tsuji, Taro,Tanaka, Takafumi,Tanaka, Tsukushi,Yazaki, Ryo,Ohshima, Takashi
, p. 4164 - 4170 (2020/06/04)
We developed a catalytic aerobic method to synthesize α,α-disubstituted α-amino acids through cross-dehydrogenative coupling of azlactones. Combining an iron catalyst with a bisoxazolidine ligand resulted in high catalytic performance, and cross-coupling with an indole proceeded smoothly under aerobic conditions. A wide variety of α-aryl and aliphatic amino acid derived azlactones were applied to the present catalysis. In addition, a quaternary carbon could be constructed using oxindole and benzofuranone under aerobic conditions.
Boron-Catalyzed α-Amination of Carboxylic Acids
Morisawa, Takuto,Sawamura, Masaya,Shimizu, Yohei
, p. 7466 - 7469 (2019/10/02)
A boron-catalyzed α-amination of simple carboxylic acids was developed. Catalytically generated boron enolates of carboxylic acids reacted with an electrophilic aminating reagent, diisopropylazodicarboxylate, to provide amino acid derivatives. The catalysis afforded not only α-monosubstituted glycine derivatives but also α,α-disubstituted derivatives. The resulting α-aminocarboxylic acid was easily converted to carboxylic acid derivatives. Extension to a catalytic asymmetric variant was possible by introducing a chiral ligand on the boron catalyst.
Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer
Tanaka, Takafumi,Tanaka, Tsukushi,Tsuji, Taro,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 3541 - 3544 (2018/06/26)
A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.
Ru-catalyzed C[sbnd]H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
Ruiz, Sara,Sayago, Francisco J.,Cativiela, Carlos,Urriolabeitia, Esteban P.
, p. 407 - 418 (2016/12/16)
The reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl2]2 (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl2]2 (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).
Rh-catalyzed asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution
Fan, Dongyang,Lu, Jian,Liu, Yang,Zhang, Zhenfeng,Liu, Yangang,Zhang, Wanbin
, p. 5541 - 5547 (2016/08/05)
Catalyzed by a rhodium complex of P-stereogenic diphosphine ligand trichickenfootphos (TCFP), asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution has been realized for the preparation of chiral arylglycines with good yields and enantioselectivities.
COMPOUNDS WHICH INHIBIT THE GLYCINE TRANSPORTER AND USES THEREOF
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Page/Page column 52, (2008/06/13)
Compounds of formula (I) and salts and solvates thereof are provided: wherein R1 to R8 and n are defined in the description. Uses of the compounds as medicaments, and in the manufacture of medicament for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder are also disclosed. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.
Synthesis of o,p-EDDHA and its detection as the main impurity in o,o-EDDHA commercial iron chelates
Gomez-Gallego, Mar,Sherra, Miguel A.,Alcazar, Roberto,Ramirez, Pedro,Pinar, Carmen,Mancheno, Maria Jose,Garcia-Marco, Sonia,Yunta, Felipe,Lucena, Juan Jose
, p. 6395 - 6399 (2007/10/03)
Ethylenediamine-N,N′bis(o-hydroxyphenyl) acetic acid (o,o-EDDHA) is one of the most efficient iron chelates employed to relieve iron chlorosis in plants. However, the presence of positional isomers of EDDHA in commercial iron chelates has been recently demonstrated, and among them, it has been claimed that ethylenediamine-N(o-hydroxyphenylacetic)-N′(p-hydroxyphenylacetic) acid (o,p-EDDHA) is the main impurity present in EDDHA fertilizers. Here we report the preparation of o,p-EDDHA, a compound whose synthesis had not been previously reported. The synthetic o,p-EDDHA is able to form ferric complexes, and it has been used as a standard in the analysis of the impurities of commercial iron fertilizers. The presence of o,p-EDDHA/Fe3+ in commercial samples has been unambiguously demonstrated by HPLC.
