1374027-59-4Relevant academic research and scientific papers
Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α-Tertiary Amino Ketones from Sulfonium Ylides
Guo, Wengang,Li, Pingfan,Luo, Yuzheng,Sun, Jianwei,Sung, Herman H.-Y.,Williams, Ian D.
supporting information, p. 14384 - 14390 (2020/09/15)
Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-Amino ketones, which is particularly useful for the less accessible acyclic α-Tertiary cases. By a protonation-Amination sequence, our approach represents a rare asymmetric H-heteroatom bond insertion by α-carbonyl sulfonium ylides, an attractive surrogate of diazocarbonyls. The mild intermolecular C-N bond formation was catalyzed by chiral phosphoric acids with excellent efficiency and enantioselectivity. The products are precursors to other important chiral amine derivatives, including drug molecules and chiral ligands. The enantioselectivity was controlled by dynamic kinetic resolution in the amination step, rather than the initial protonation. This process opens up a new platform for the development of other related insertion reactions.
Synthesis of enantiomerically-enriched N-aryl amino-amides via a Jocic-type reaction
Hobson, Christian,Perryman, Michael S.,Kirby, Gavin,Clarkson, Guy J.,Fox, David J.
supporting information, p. 3965 - 3968 (2018/10/02)
Enantiomerically-enriched secondary trichloromethyl-alcohols react with aryl amines to give enantiomerically-enriched α-N-arylamino-acid derivatives. The intermediate acid chlorides can react in situ with aryl or, regioselectively, with alkyl amines to gi
Direct Aryl C?H Amination with Primary Amines Using Organic Photoredox Catalysis
Margrey, Kaila A.,Levens, Alison,Nicewicz, David A.
supporting information, p. 15644 - 15648 (2017/11/20)
The direct catalytic C?H amination of arenes is a powerful synthetic strategy with useful applications in pharmaceuticals, agrochemicals, and materials chemistry. Despite the advances in catalytic C?H functionalization, the use of aliphatic amine coupling partners is limited. Described herein is the construction of C?N bonds, using primary amines, by direct C?H functionalization with an acridinium photoredox catalyst under an aerobic atmosphere. A wide variety of primary amines, including amino acids and more complex amines are competent coupling partners. Various electron-rich aromatics and heteroaromatics are useful scaffolds in this reaction, as are complex, biologically active arenes. We also describe the ability to functionalize arenes that are not oxidized by an acridinium catalyst, such as benzene and toluene, thus supporting a reactive amine cation radical intermediate.
Synthesis of some n-aryl α-Amino acids using diaryliodonium salts
Mckerrow, Jason D.,Al-Rawi, Jasim M.,Brooks, Peter
, p. 1227 - 1236 (2012/09/22)
Bis[(3'-methoxycarbonyl)phenyl]iodonium bromide (4a), bis (4'-methoxyphenyl)iodonium iodide (4b) and bis (4'-acetamidophenyl)iodonium iodide (4c) were employed for the first time in the arylation of α-amino acid methyl esters. Yields of the synthesised products 5, 6 and 7 were good to high. These were then hydrolyzed to the corresponding N-aryl α-amino acids 8 and 9. The chiral integrity of the amino acids was maintained throughout the reaction sequence as confirmed by the synthesis of chiral tripeptide 10 and dipeptides 11. The structures of the new compounds were confirmed by IR, 1H and 13C NMR in addition to CHN microanalysis or high resolution mass spectrometry.
