54220-18-7Relevant academic research and scientific papers
Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
Chen, Dong-Huang,Sun, Wei-Ting,Zhu, Cheng-Jie,Lu, Guang-Sheng,Wu, Dong-Ping,Wang, Ai-E,Huang, Pei-Qiang
, p. 8827 - 8831 (2021/03/16)
The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.
Benzhydrylamine: An effective aminating agent for the synthesis of primary amines
Sun, Quan-Wei,Xing, Jun-De,Qin, Yu-Hong,Yin, Xu-Wen,Zhou, Yi
, p. 181 - 183 (2018/05/26)
Aldehydes, ketones, alkyl toluene-p-sulfonates and halides are converted into the corresponding primary amines with benzhydrylamine as a valuable ammonia synthon in moderate to excellent yields.
Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide
Guo, Chun-Xiao,Zhang, Wen-Zhen,Zhou, Hui,Zhang, Ning,Lu, Xiao-Bing
supporting information, p. 17156 - 17159 (2016/11/23)
A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.
A biosynthesis-inspired approach to over twenty diverse natural product-like scaffolds
Firth, James D.,Craven, Philip G. E.,Lilburn, Matthew,Pahl, Axel,Marsden, Stephen P.,Nelson, Adam
supporting information, p. 9837 - 9840 (2016/08/04)
A synthetic approach to diverse scaffolds was developed that was inspired by diterpene biosynthesis. Initial scaffolds, generated using Diels-Alder reactions of furyl-functionalised amines, were transformed into alternative scaffolds using cleavage, ring expansion, annulation and rearrangement reactions. In total, 25 diverse scaffolds were prepared that were shown to have high natural product-likeness.
Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung
Blume, Fabian,Albeiruty, Mhd Haitham,Deska, Jan
, p. 2093 - 2099 (2015/07/15)
Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by ω-transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.
Dimethyl (2-Furyl)-N-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs
Klimczak, Anna Agnieszka,Matusiak, Agnieszka,Lewkowski, Jaroslaw,Bitner, Jan,Szemraj, Janusz,Kontek, Renata
, p. 1088 - 1099 (2015/08/04)
Cytotoxicities of several new aminophosphonic compounds bearing 2-furyl moiety 2b-d and 3a-c on KYSE 30, 150, and 270 esophageal cancer cell lines are reported here. The qualitative study on correlations between the structure and cytotoxic activity of fur
Phytotoxicity of new furan-derived aminophosphonic acids, N -Aryl furaldimines and 5-nitrofuraldimine
Matusiak, Agnieszka,Lewkowski, Jaroslaw,Rychter, Piotr,Biczak, Robert
, p. 7673 - 7678 (2013/09/02)
The aim of this work was to synthesize selected furaldimines and their aminophosphonic derivatives and evaluation the phytotoxicity of new obtained products according to OECD 208 Guideline. Four Schiff bases, N-furfurylidene-p-anisidine (1a), N-furfurylid
Application of bis(trimethylsilyl) phosphonite in the efficient preparation of new heterocyclic -aminomethyl- H -phosphinic acids
Olszewski, Tomasz K.,Boduszek, Bogdan
experimental part, p. 437 - 442 (2011/04/22)
A simple, reproducible, and efficient preparation of new heterocyclic -aminomethyl-H-phosphinic acids is reported. The synthetic protocol is based on the application of bis(trimethylsilyl) phosphonite, as an efficient phosphorous nucleophile, in the reaction with the corresponding heterocyclic imines. Subsequent methanolysis of the addition intermediates leads to the expected heterocyclic -aminomethyl-H-phosphinic acids in fair to good yields. Additionally, acidic hydrolysis of benzhydrylamino derivatives allows the efficient preparation of free -aminomethyl-H-phosphinic acids in good yields and high purity after simple crystallization. Georg Thieme Verlag Stuttgart New York.
Catalytic asymmetric Strecker hydrocyanation of imines using Yb(OTf) 3-pybox catalysts
Karimi, Babak,Maleki, Aziz
supporting information; experimental part, p. 5180 - 5182 (2009/12/08)
We have explored the highly enantioselective Strecker hydrocyanation of a wide range of aromatic, α,β-unsaturated, heterocyclic, and aliphatic aldimines with good to excellent conversions and ees up to 98% in the presence of catalytic amounts of Yb(OTf)s
1-Amino-1-aryl- and 1-amino-1-heteroaryl-methanephosphonic acids and their n-benzhydryl-protected diethyl esters: Preparation and characterization
Hudson, Harry R.,Lee, Rosalind J.,Matthews, Ray W.
, p. 1691 - 1709 (2007/10/03)
N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1′-naphthyl, 9′-anthryl, 1′-pyrenyl) and 1-amino-1-heteroaryl- (furyl, 2′-thienyl, 3′-thienyl, 2′-pyrrolyl)-methanephosphonic acids, prepared by the
