130378-43-7Relevant academic research and scientific papers
Synthesis and Applications of Unquaternized C-Bound Boron Enolates
Ng, Elvis Wang Hei,Low, Kam-Hung,Chiu, Pauline
, p. 3537 - 3541 (2018/03/21)
A general and facile method to prepare unquaternized C-bound boron enolates by a ligand-controlled O-to-C isomerization is reported. Using this protocol, C-bound pinacolboron enolates have been isolated in pure form for the first time, and have been fully characterized by NMR spectroscopy and X-ray crystallography. In contrast to the general perception, such C-boron enolates are stable without coordinative saturation at the boron. Moreover, C-boron enolates present reactivities that are distinct from the O-boron enolates, and their applications in C-O and C-C bond formations are demonstrated.
Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases
Sandoval, Braddock A.,Meichan, Andrew J.,Hyster, Todd K.
supporting information, p. 11313 - 11316 (2017/08/30)
Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.
A new method for production of chiral 2-aryl-2-fluoropropanoic acids using an effective kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids
Tengeiji, Atsushi,Shiina, Isamu
experimental part, p. 7356 - 7378 (2012/09/05)
We report a new method for the preparation of chiral 2-aryl-2- fluoropropanoic acids, including 2-fluoroibuprofen, a fluorinated analogue of non-steroidal anti-inflammatory drugs (NSAIDs), by the kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids using enantioselective esterification. By applying pivalic anhydride (Piv2O) as a coupling agent, bis(α-naphthyl)methanol [(α-Np)2CHOH] as an achiral alcohol, and (+)-benzotetramisole (BTM) as a chiral acyl-transfer catalyst, a series of racemic 2-aryl-2-fluoropropanoic acids were kinetically separated to afford the optically active carboxylic acids and the corresponding esters with good to high enantiomeric excesses. This technology can provide a convenient approach to furnish the chiral a-fluorinated drugs containing quaternary carbons at the α-positions in the 2-aryl-2-fluoropropanoic acid structure.
Pd-catalyzed decarboxylative cross-couplings of potassium malonate monoesters with aryl halides
Feng, Yi-Si,Wu, Wei,Xu, Zhong-Qiu,Li, Yan,Li, Ming,Xu, Hua-Jian
, p. 2113 - 2120 (2012/03/26)
An efficient catalytic protocol for Pd-catalyzed decarboxylative cross-coupling of potassium malonate monoesters and derivatives with aryl bromides and chlorides are described. Because of its broad applicability, this new catalytic system provides an alternative method for the preparation of diverse aryl acetic acids and derivatives.
Exclusive aromatic vs aliphatic C-H bond functionalization by carbene insertion with gold-based catalysts
Rivilla, Ivan,Gomez-Emeterio, B. Pilar,Fructos, Manuel R.,Diaz-Requejo, M. Mar,Perez, Pedro J.
experimental part, p. 2855 - 2860 (2011/07/08)
The direct functionalization of aromatic C-H bonds by carbene insertion from diazo compounds catalyzed by gold complexes with N-heterocyclic ligands is described. The reaction is completely selective toward the C sp2-H bonds, other C sp3-H bonds remaining unreacted. A study with several NHC ligands in Au(I) and Au(III) complexes has been performed. The potential application of this strategy to give profen derivatives has also been explored.
NOVEL ADENINE COMPOUND AND USE THEREOF
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Page/Page column 28, (2010/02/12)
A drug for topically administration which is effective as an antiallergic agent. The drug for topically administration contains as an active ingredient an adenine compound represented by the general formula (1): [wherein ring A represents a 6 to 10 membered, mono or bicyclic, aromatic hydrocarbon or a 5 to 10 membered, mono or bicyclic, aromatic heterocycle containing one to three heteroatoms selected among 0 to 2 nitrogen atoms, 0 or 1 oxygen atom, and 0 or 1 sulfur atom; n is an integer of 0 to 2; m is an integer of 0 to 2; R represents halogeno, (un)substituted alkyl, etc.; X1 represents oxygen, sulfur, NR1 (R1 represents hydrogen or alkyl), or a single bond; Y1 represents a single bond, alkylene; etc.; Y2 represents a single bond, alkylene, etc.; Z represents alkylene; and at least one of Q1 and Q2 represents -COOR10 (wherein R10 represents (un)substituted alkyl, etc.), etc.] or a pharmaceutically acceptable salt of the compound.
