65501-30-6Relevant academic research and scientific papers
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides
Zhang, Rui,Zhang, Zhikun,Zhou, Qi,Yu, Lefei,Wang, Jianbo
, p. 5744 - 5748 (2019)
Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the
Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis
Nagib, David A.,Rafferty, Sean M.,Rutherford, Joy E.,Wang, Lu,Zhang, Lumin
supporting information, p. 5622 - 5628 (2021/05/07)
A cross-selective aza-pinacol coupling of aldehydes and imines has been developed to afford valuable β-amino alcohols. This strategy enables chemoselective conversion of aliphatic aldehydes to ketyl radicals, in the presence of more easily reduced imines and other functional groups. Upon carbonyl-specific activation by AcI, a photoinitiated Mn catalyst selectively reduces the resulting α-oxy iodide by an atom transfer mechanism. The ensuing ketyl radical selectively couples to imines, precluding homodimerization by a classical reductive approach. In this first example of reductive, ketyl coupling by atom transfer catalysis, Zn serves as a terminal reductant to facilitate Mn catalyst turnover. This new strategy also enables ketyl radical couplings to alkenes, alkynes, aldehydes, propellanes, and chiral imines.
A multicomponent approach to the synthesis of N-sulfonyl β2,3-amino esters
Gall, Erwan Le,Sengmany, Stephane,Samb, Issa,Benakrour, Sabrina,Colin, Christopher,Pignon, Antoine,Leonel, Eric
supporting information, p. 3423 - 3426 (2014/05/20)
The multicomponent synthesis of α,β-disubstituted N-sulfonyl β-amino esters is described. It involves a zinc-mediated, cobalt-catalyzed three-component reaction between sulfonylimines, acrylates and organic bromides. A possible mechanism is proposed, emph
Fluorinated aromatic ketones as nucleophiles in the asymmetric organocatalytic formation of C-C and C-N bonds: A facile route to the construction of fluorinated quaternary stereogenic centers
Zhao, Yujun,Pan, Yuanhang,Liu, Hongjun,Yang, Yuanyong,Jiang, Zhiyong,Tan, Choon-Hong
supporting information; experimental part, p. 3571 - 3574 (2011/05/05)
Highly enantioselective Mannich and α-amination reactions have been successfully developed using α-fluorinated aromatic ketones as fluorocarbon nucleophiles in the presence of a bicyclic chiral guanidine (see scheme; Ms=methanesulfonyl). This method is a
Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide
Kantam, M. Lakshmi,Mahendar, Koosam,Sreedhar, Bojja,Choudary, Boyapati. M.,Bhargava, Suresh K.,Priver, Steven H.
experimental part, p. 5042 - 5052 (2010/08/20)
The Mannich-type reaction between alkyl, aryl and heterocyclic aldimines and sulfonium salts for the synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide (NAP-MgO) is described. These products are obtained in moderate to high yields with moderate diastereoselectivities. The configuration of ethyl-3-{[(4-methylphenyl)sulfonyl] amino}-2-(methylsulfanyl)-3-(4-nitrophenyl)propanoate (major isomer) has been confirmed by X-ray diffraction technique to be anti, and consistent with the assignment based on 1H NMR spectroscopy. These α-sulfanyl- β-amino acid derivatives are important building blocks for pharmaceuticals with potent biological activity.
