104201-65-2Relevant articles and documents
Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis
Ma, Jiguo,Zhou, Qinghai,Song, Guanshui,Song, Yongchang,Zhao, Guoqing,Ding, Kuiling,Zhao, Baoguo
supporting information, p. 10588 - 10592 (2021/04/06)
Direct α-functionalization of NH2-free glycinates with relatively weak electrophiles such as α,β-unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α-C of glycinate 1 a with α,β-unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 % yields with 81–97 % ee's after in situ lactamization. The trans and cis diastereomers can be obtained at the same time by chromatography and both of them can be easily converted into chiral 4-substituted pyrrolidin-2-ones such as Alzheimer's drug Rolipram (11) with the same absolute configuration via tert-butyl group removal and subsequent Barton decarboxylation.
Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination
Wang, Mei-Ling,Xu, Hui,Li, Han-Yuan,Ma, Biao,Wang, Zhen-Yu,Wang, Xing,Dai, Hui-Xiong
supporting information, p. 2147 - 2152 (2021/04/05)
Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.
Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).
A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Smith, Emily G.,Cambeiro, Xacobe C.
supporting information, p. 5383 - 5388 (2021/07/26)
A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.
HETEROCYCLIC COMPOUNDS FOR MODULATING NR2F6
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Paragraph 00393; 00405, (2021/09/04)
The present disclosure relates to compounds capable of modulating the activity of NR2F6. The compounds of the disclosure may be used in methods for the prevention and/or the treatment of diseases and disorders associated with modulating NR2F6 activity.
Bis(imidazolium) chloride based on 1,2-phenylenediamine as efficient ligand precursor for palladium-catalyzed Mizoroki-Heck cross-coupling reaction
Takallou, Ahmad,Habibi, Azizollah,Halimehjani, Azim Ziyaei,Balalaie, Saeed
supporting information, p. 24 - 28 (2019/03/21)
Bis(imidazolium) chlorides based on 1,2-phenylenediamine were introduced as efficient ligand precursors in the Pd-catalyzed Mizoroki-Heck cross-coupling reactions of substituted aryl halides with activated alkenes to afford the corresponding functionalized alkenes. While high to excellent yields (78–96%) were obtained with aryl bromides, moderate yields (51–59%) were achieved for aryl chlorides in this protocol.
Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles
Sofiadis, Manolis,Kalaitzakis, Dimitris,Sarris, John,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
supporting information, p. 6742 - 6746 (2019/04/13)
A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2-enones with α,β-unsaturated aldehydes has been developed. The organocatalysed [3+3]-annulations proceed with high levels of regio-, diastereo-, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).
Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
Liu, Jiawang,Dong, Kaiwu,Franke, Robert,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias
supporting information, p. 10282 - 10288 (2018/08/03)
A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.
Magnetic dendritic polymer nanocomposites as supports for palladium: A highly efficient and reusable catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions
Ma, Rong,Yang, Pengbo,Bian, Fengling
, p. 4748 - 4756 (2018/03/21)
A novel catalyst Fe3O4@SiO2-Dendrimer-Pd based on palladium immobilized on magnetic dendritic polymer nanocomposites was successfully synthesized and characterized by FT-IR, EA, XRD, TEM, EDX, VSM and XPS. This nanocatalyst showed excellent catalytic activity for solvent-free Mizoroki-Heck reaction and Suzuki-Miyaura reaction in EtOH/H2O at a palladium loading of only 0.009 mol%. Moreover, the Fe3O4@SiO2-Dendrimer-Pd catalyst could be conveniently recovered by an external magnet and used consecutively five times with excellent yields. The remarkable catalytic performances and convenient magnetic separability of the Fe3O4@SiO2-Dendrimer-Pd catalyst make it promising for practical application.
SUBSTITUTED DIHYDROPYRROLOPYRAZOLE COMPOUND
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Paragraph 1051-1053, (2017/09/12)
Provided is a compound represented by formula (I) or a pharmacologically acceptable salt thereof: wherein L1 is an optionally substituted C1-6 alkylene group or the like, L2 is a single bond or the like, L3 is a single bond or the like, R1, R2, and R3 are each independently an optionally substituted C1-4 alkyl group or the like, R4 is a hydrogen atom or the like, and R5 is a hydrogen atom or the like.
