31612-63-2Relevant academic research and scientific papers
Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides
Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu
supporting information, p. 513 - 518 (2019/01/14)
Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.
One-Pot Three-Step Consecutive Transformation of L-α-Amino Acids to (R)- and (S)-Vicinal 1,2-Diols via Combined Chemical and Biocatalytic Process
Zhang, Jian-Dong,Zhao, Jian-Wei,Gao, Li-Li,Zhao, Jing,Chang, Hong-Hong,Wei, Wen-Long
, p. 5032 - 5037 (2019/10/28)
Optically pure vicinal 1,2-diols are versatile chiral building blocks in the fine chemical and pharmaceutical industries. L-α-amino acid is a good feedstock source for high value-added product production since it is inexpensive and renewable. However, conversion of L-α-amino acids to enantioenriched vicinal 1,2-diols remains a significant challenge. In this study, combining a simple chemical process and a three-enzyme cascade biocatalysis system, we have successfully implemented a one-pot sequential process for the transformation of L-α-amino acids into enantiopure vicinal 1,2-diols in aqueous medium. Firstly, the NaBH4-H2SO4 system converted L-α-amino acids to (S)-amino alcohols via amino acid carboxyl reduction. Secondly, the three-enzyme (transaminase, carbonyl reductase and glucose dehydrogenase) cascade biocatalysis system converted amino alcohols to enantiopure vicinal 1,2-diols via amino alcohol deamination, α-hydroxy ketone asymmetric reduction and cofactor regeneration. Taking advantage of the two different reaction systems, chiral vicinal 1,2-diols could be obtained from L-α-amino acids with high yields (69–90 %) and excellent ee values (91–>99 % ee).
SUBSTITUTED 4-AMINOBENZAMIDES AS KCNQ2/3 MODULATORS
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Page/Page column 147; 149, (2013/11/05)
The invention relates to substituted 4-aminobenzamides, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
SUBSTITUTED 4-AMINOBENZAMIDES AS KCNQ2/3 MODULATORS
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Paragraph 0721, (2013/11/05)
Substituted 4-aminobenzamides, pharmaceutical compositions containing these compounds and also methods of using these compounds in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes
Coombs, John R.,Haeffner, Fredrik,Kliman, Laura T.,Morken, James P.
supporting information, p. 11222 - 11231 (2013/08/23)
The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion into a Pt-B bond. Density functional theory analysis, combined with other experimental data, suggests that the insertion reaction positions platinum at the internal carbon of the substrate. A stereochemical model for this reaction is advanced that is in line both with these features and with the crystal structure of a Pt-ligand complex.
A flexible synthesis of C33-C39 polyketide region of apratoxin: Synthesis of natural and unnatural analogues
Gilles, Arnaud,Martinez, Jean,Cavelier, Florine
scheme or table, p. 437 - 440 (2012/03/22)
A flexible synthesis sequence toward the synthesis of the polyketide region of apratoxin has been developed. The common step of the synthesis is a crotylation reaction. Stereospecific aldolisation, sulfate ring opening or Jacobsen HKR is also highlighted. This synthetic scheme led to the synthesis of several analogues. These examples raise the possibility of synthesising numerous analogues of this portion of apratoxins. Then, together with our supported strategy to synthesise the oxazoline analogue of apratoxin A, this paper opens the possibility to provide easily oxoapratoxin analogues for future SAR studies of this potent antitumoral compound.
Pt-catalyzed enantioselective diboration of terminal alkenes with B 2(pin)2
Kliman, Laura T.,Mlynarski, Scott N.,Morken, James P.
supporting information; experimental part, p. 13210 - 13211 (2010/01/30)
(Chemical Equation Presented) The Pt-catalyzed enantioselective addition of bis(pinacolato)diboron to simple monosubstituted alkenes is described. This reaction occurs in the presence of a readily available chiral phosphonite ligand and is effective with a variety of terminal alkene substrates. Importantly, the reaction can operate with catalyst loadings of only 1 mol % Pt. While oxidation of the intermediate 1,2-bis(boronate) ester provides the chiral 1,2-diol as the reaction product, the intermediate may also be subjected to homologation/oxidation to furnish a chiral 1,4-diol as the reaction product.
Highly diastereoselective synthesis of orthoquinone monoketals through λ13-iodane-mediated oxidative dearomatization of phenols
Pouysegu, Laurent,Chassaing, Stefan,Dejugnac, Delphine,Lamidey, Anne-Marie,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Quideau, Stephane
supporting information; experimental part, p. 3552 - 3555 (2009/02/07)
(Chemical Equation Presented) Versatile chiral substrates for asymmetric synthesis are formed through the spiroketalization of phenols with a chiral substituted ethanol unit O-tethered to the ortho position upon treatment with PhI-(OAc)2 (see example; TFE = 2,2,2-tri-fluoroethanol). Intermediates with a six-membered iodine(III)-containing ring (the natural localized molecular orbitals associated with the I-C6 bond are shown) undergo ligand coupling to give the spiroketals.
