- Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes
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The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat
- Carminati, Daniela M.,Decaens, Jonathan,Couve-Bonnaire, Samuel,Jubault, Philippe,Fasan, Rudi
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p. 7072 - 7076
(2021/02/27)
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- A CO2-Catalyzed Transamidation Reaction
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Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2
- Yang, Yang,Liu, Jian,Kamounah, Fadhil S.,Ciancaleoni, Gianluca,Lee, Ji-Woong
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p. 16867 - 16881
(2021/11/18)
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- Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water
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Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.
- Abe, Manabu,Akita, Munetaka,Chitose, Youhei,Hyodo, Yuki,Koike, Takashi,Takahashi, Keigo,Yoshizawa, Michito
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supporting information
(2021/10/21)
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- Metabolically stable vanillin derivatives for the treatment of hypoxia
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Vanillin derivative compounds that bind covalently with hemoglobin are provided. Methods of treating sickle cell disease and other hypoxia-related disorders by administering such compounds are also provided.
- -
-
Page/Page column 12; 15-16
(2021/09/01)
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- Phase-Transfer Catalyzed Asymmetric [4 + 1] Annulations for the Synthesis of Chiral 2,2-Disubstituted Tetrahydrothiophenes
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An efficient catalytic asymmetric [4 + 1] reaction, which features the use of simple β-keto esters as one-carbon nucleophiles and 5-succinimidothio-pent-2-enoates as four-atom bielectrophiles, has been developed in the presence of a bifunctional chiral ph
- Yin, Qi,Wen, Xiaolu,Chen, Yiwei,Gong, Xiangnan,Hu, Lin
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supporting information
p. 7529 - 7534
(2021/10/02)
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- Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination
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Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.
- Tan, Xuefeng,Massignan, Leonardo,Hou, Xiaoyan,Frey, Johanna,Oliveira, Jo?o C. A.,Hussain, Masoom Nasiha,Ackermann, Lutz
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supporting information
p. 13264 - 13270
(2021/05/06)
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- Quinolin-8-yl Formate: A New Option for Small-Scale Carbonylation Reactions in Microwave Reactors
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A convenient procedure for conducting small-scale carbonylations of aryl or benzyl halides in a microwave reactor by using quinolin-8-yl formate is described. The resulting 8-acyloxyquinolines were shown to be more reactive than phenyl esters in acyl-tran
- Maddocks, Christopher J.,Aathimanikandan, Sivakumar V.,Richardson, Jeffery,Ruble, J. Craig
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p. 1608 - 1612
(2020/09/09)
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- Br?nsted Base-Catalyzed Transformation of α,β-Epoxyketones Utilizing [1,2]-Phospha-Brook Rearrangement for the Synthesis of Allylic Alcohols Having a Tetrasubstituted Alkene Moiety
-
A stereoselective transformation of α,β-epoxyketones into alkenylphosphates having a hydroxymethyl group on the β-carbon was established by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. The reaction involves the catalytic generation of an α-oxygenated carbanion located at the α-position of an epoxide moiety through the [1,2]-phospha-Brook rearrangement and the following epoxide opening. Further transformation of the alkenylphosphates by the palladium-catalyzed cross-coupling reaction with Grignard reagents provided allylic alcohols having a stereodefined all-carbon tetrasubstituted alkene moiety.
- Kondoh, Azusa,Tasato, Naoko,Aoki, Takuma,Terada, Masahiro
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supporting information
p. 5170 - 5175
(2020/07/04)
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- Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO
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We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.
- Johansen, Martin B.,Gedde, Oliver R.,Mayer, Thea S.,Skrydstrup, Troels
-
supporting information
p. 4068 - 4072
(2020/06/03)
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- An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
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The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.
- Bauer, Adriano,Di Mauro, Giovanni,Li, Jing,Maulide, Nuno
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p. 18208 - 18212
(2020/08/21)
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- Synthesis of various acylating agents directly from carboxylic acids
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A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
- Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
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supporting information
p. 1622 - 1632
(2020/04/27)
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- An investigation of structure‐activity relationships of azolylacryloyl derivatives yielded potent and long‐acting hemoglobin modulators for reversing erythrocyte sickling
-
Aromatic aldehydes that bind to sickle hemoglobin (HbS) to increase the protein oxygen affinity and/or directly inhibit HbS polymer formation to prevent the pathological hypoxia‐induced HbS polymerization and the subsequent erythrocyte sickling have for s
- Abdulmalik, Osheiza,El‐araby, Moustafa E.,Ghatge, Mohini S.,Muhammad, Yosra A.,Omar, Abdelsattar M.,Paredes, Steven D.,Safo, Martin K.
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- Structurally Diverse Acyl Bicyclobutanes: Valuable Strained Electrophiles
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Bicyclo[1.1.0]butanes (BCBs) are highly strained carbocycles that have emerged as versatile synthetic tools, particularly for the construction of functionalized small molecules. This work reports two efficient pathways for the rapid preparation of over 20 structurally diverse BCB ketones, encompassing simple alkyl and aryl derivatives, as well as unprecedented amino acid, dipeptide, bioisostere, and bifunctional linchpin reagents currently inaccessible using literature methods. Analogues are readily forged in two steps and in high yields from simple carboxylic acids or through unsymmetrical ketone synthesis beginning with a convenient carbonyl dication equivalent. The utility of this novel toolbox of strained electrophiles for the selective modification of proteinogenic nucleophiles is highlighted.
- Attard, Riley H.,Gardiner, Michael G.,Malins, Lara R.,Schwartz, Brett D.,Zhang, Meng Yao
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supporting information
p. 2808 - 2812
(2020/03/04)
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- Iron-Catalyzed, Iminyl Radical-Triggered Cascade 1,5-Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five-Atom Assembling Unit
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By integration of iminyl radical-triggered 1,5-hydrogen atom transfer and (5+2) or (5+1) annulation processes, a series of structurally novel and interesting azepine and spiro-tetrahydropyridine derivatives have been successfully prepared in moderate to good yields. This method utilizes FeCl2 as the catalyst and readily available oximes as five-atom units, while showcasing broad substrate scope and good functional group compatibility. The annulation products can be easily converted into many valuable compounds. Moreover, DFT calculation studies are performed to provide some insights into the possible reaction mechanisms for the (5+2) and (5+1) annulations.
- Chen, Ying-Chun,Du, Fei,Jiang, Kun,Liang, Wu,Ouyang, Qin,Shuai, Li,Wei, Ye,Yang, Jie
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supporting information
p. 19222 - 19228
(2020/08/25)
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- Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines
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Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.
- Gim, Hyo Jin,Jung, Michael E.
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supporting information
p. 2548 - 2552
(2019/06/08)
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- Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives
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The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines is reported. These aldimines react with Weinreb amides, ketones, or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allows for an efficient synthesis of 1,2-dicarbonyl compounds and α-hydroxy ketones.
- Schw?rzer, Kuno,Bellan, Andreas,Z?schg, Maximilian,Karaghiosoff, Konstantin,Knochel, Paul
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supporting information
p. 9415 - 9418
(2019/05/10)
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- Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
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A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
- Huang, Fei,Zhang, Songlin
-
supporting information
p. 7430 - 7434
(2019/10/11)
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- Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
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An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
- Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
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supporting information
p. 5098 - 5102
(2018/09/13)
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- COMPOUNS, COMPOSITIONS AND METHODS OF USE
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Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.
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Page/Page column 160; 161
(2018/07/29)
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- Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition
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The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a
- Ningegowda, Raghu,Bhaskaran, Savitha,Sajith, Ayyiliath M.,Aswathanarayanappa, Chandrashekar,Padusha, M. Syed Ali,Priya, Babu Shubha
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- Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
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A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
- Das, Riki,Kapur, Manmohan
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p. 1114 - 1126
(2018/06/18)
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- Compounds for inflammation and immune-related uses
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The invention relates to certain compounds or pharmaceutically acceptable salts, solvates, clathrates, or prodrugs thereof, that are useful as immunosuppressive agents and for treating and preventing inflammatory conditions, allergic disorders, and immune disorders.
- -
-
Page/Page column 196-197
(2017/05/10)
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- N-Methoxy-N-methylcyanoformamide, a Highly Reactive Reagent for the Formation of β-Keto Weinreb Amides and Unsymmetrical Ketones
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A rapid and straightforward synthesis of the new and highly reactive reagent N-methoxy-N-methylcyanoformamide from trimethylsilyl cyanide and N-methoxy-N-methylcarbamoylimidazole, is reported. This reagent enables the one-pot preparation of β-carbonyl Wei
- Nugent, Jeremy,Schwartz, Brett D.
-
supporting information
p. 3834 - 3837
(2016/08/16)
-
- A new strategy for accessing (S)-1-(furan-2-yl)pent-4-en-1-ol: a key precursor of Ipomoeassin family of compounds and C1–C15 domain of halichondrins
-
A highly efficient synthesis of (S)-1-(furan-2-yl)pent-4-en-1-ol, known to be an initial precursor of Ipomoeassin family of compounds and C1–C15 domain of halichondrins has been achieved via a sequence involving the use of Weinreb amide formation followed by Weinreb ketone synthesis and finally CBS (Corey–Bakshi–Shibata) reduction. Detailed study on improvement of each step is described. The title compound was converted to a potential cytotoxic agent for further pharmacological studies.
- Jammula, Subba Rao,Anna, Venkateswara Rao,Tatina, Sudhakar,Krishna, Thalishetti,Sreenivas, B. Yogi,Pal, Manojit
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supporting information
p. 3924 - 3928
(2016/08/09)
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- SMALL MOLECULE LFA-1 INHIBITORS
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The present invention relates to novel compounds which are capable of inhibiting the interaction of LFA-1 with its counter ligands.
- -
-
Page/Page column 120
(2016/01/01)
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- One-Pot Direct Synthesis of Weinreb Amides from Aryl and Hetero Aryl Halides Using Co 2(CO) 8 as an Effective CO Source under Conventional Thermal Heating
-
A successful protocol for the synthesis of Weinreb amides directly from aryl halides via aminocarbonylation with N,O-dimethyl hydroxylamine using Co2(CO)8 as an in situ CO source has been demonstrated. The effects of various reaction parameters such as temperature, base, and CO source have also been investigated and optimized. GRAPHICAL ABSTRACT.
- Baburajan, Poongavanam,Elango, Kuppanagounder P.
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p. 541 - 548
(2015/10/29)
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- One-pot Unsymmetrical Ketone Synthesis Employing a Pyrrole-Bearing Formal Carbonyl Dication Linchpin Reagent
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A one-pot procedure for the synthesis of unsymmetrical ketones utilizing a pyrrole-bearing carbonyl linchpin reagent (carbonyl linchpin N,O-dimethylhydroxylamine pyrrole; CLAmP) is reported. In contrast to other carbonyl dielectrophile equivalents, CLAmP enables the synthesis of ketones from a variety of organolithium and Grignard reagents. The electrophilic nature of CLAmP enables the addition of less reactive as well as thermally unstable nucleophiles. CLAmP was designed to form kinetically stable tetrahedral intermediates upon the addition of organometallic nucleophiles. Evidence for the existence of persistent tetrahedral intermediates was obtained through in situ IR studies.
- Heller, Stephen T.,Newton, James N.,Fu, Tingting,Sarpong, Richmond
-
supporting information
p. 9839 - 9843
(2015/08/19)
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- Copper-catalyzed synthesis of weinreb amides by oxidative amidation of alcohols
-
A simple and efficient protocol has been developed for the oxidative amidation of alcohols to Weinreb amides using tert-butyl hydroperoxide as an oxidant and an inexpensive and air stable copper catalyst. The present protocol is advantageous as it uses commercially affordable alcohols as starting materials. The developed protocol also tolerates various substituted alcohols as starting materials to provide good to excellent yields of the desired products.
- Yedage, Subhash L.,Bhanage, Bhalchandra M.
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p. 526 - 532
(2015/02/19)
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- Synthesis and antibacterial activities of cadiolides A, B and C and analogues
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The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.
- Boulangé, Agathe,Parraga, Javier,Galán, Abraham,Cabedo, Nuria,Leleu, Stéphane,Sanz, Maria Jesus,Cortes, Diego,Franck, Xavier
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p. 3618 - 3628
(2015/07/27)
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- Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
-
The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor-acceptor complexes of the oximes and Et3N was proposed as a key step of this process.
- Davies, Jacob,Booth, Samuel G.,Essafi, Stephanie,Dryfe, Robert A. W.,Leonori, Daniele
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supporting information
p. 14017 - 14021
(2016/01/25)
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- Reductive N-O cleavage of Weinreb amides by sodium in alumina and silica gels: synthetic and mechanistic studies
-
The use of sodium in alumina and silica gels for the reductive cleavage of the N-O bond of N-methoxy-N-methylamides, commonly referred to as Weinreb amides, has been investigated. This method reduces a diverse set of Weinreb amides with different function
- Jackson, James E.,O'Brien, Brittany N.,Kedzior, Sonya K.,Fryz, Gage R.,Jalloh, Fatmata S.,Banisafar, Arash,Caldwell, Michael A.,Braun, Max B.,Dunyak, Bryan M.,Dye, James L.
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supporting information
p. 6227 - 6230
(2015/10/20)
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- An Efficient synthesis of Weinreb amides and ketones via palladium nanoparticles on ZIF-8 catalysed carbonylative coupling
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Heterogeneously catalysed carbonylative coupling reactions such as aminocarbonylation and Suzuki-carbonylation are reported using Pd nanoparticles supported on ZIF-8 for efficient and environmentally attractive synthesis of Weinreb amides and ketones from aryl bromides or iodides. The catalyst is air stable, offers high activity with very low palladium leaching and is recyclable. The presence of a phosphine ligand was required when aryl bromides were used as substrates, while no ligand was necessary when aryl iodides were used. the Partner Organisations 2014.
- Thanh Dang, Tuan,Chen, Anqi,Majeed Seayad, Abdul
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p. 30019 - 30027
(2014/08/05)
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- Pd(OAc)2/DABCO as an efficient and phosphine-free catalytic system for the synthesis of single and double Weinreb amides by the aminocarbonylation of aryl iodides
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This work reports a mild, stable and efficient Pd(OAc)2/DABCO catalysed protocol for the synthesis of single and double Weinreb amides. Double Weinreb amides, having 1,4-phenylene- and biphenylene-linkers-important backbones for the synthesis of biologically active symmetrical resorcylate oligomer units-were synthesized by the double carbonylation of aryl diiodides. Notably, the reaction does not require any expensive or air/moisture sensitive phosphine ligands. DABCO was found to be an inexpensive and stable ligand for the Pd(OAc)2 catalysed carbonylation of aryl iodides under an atmospheric pressure of carbon monoxide, and offered excellent yields of the single and double Weinreb amides. the Partner Organisations 2014.
- Gadge, Sandip T.,Bhanage, Bhalchandra M.
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p. 5727 - 5732
(2014/07/22)
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- Design and synthesis of epicocconone analogues with improved fluorescence properties
-
Epicocconone is a natural latent fluorophore that is widely used in biotechnology because of its large Stokes shift and lack of fluorescence in its unconjugated state. However, the low photostability and quantum yields of epicocconone have limited its wid
- Peixoto, Philippe A.,Boulang, Agathe,Ball, Malcolm,Naudin, Bertrand,Alle, Thibault,Cosette, Pascal,Karuso, Peter,Franck, Xavier
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p. 15248 - 15256
(2014/12/11)
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- Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1H-isochromene derivatives through an intramolecular-cyclization/ enantioselective-reduction sequence
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The transformation of ortho-alkynylaryl ketones through a cyclization/enantioselective-reduction sequence in the presence of a chiral silver phosphate catalyst afforded 1H-isochromene derivatives in high yield with fairly good to high enantioselectivity. An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6-diene framework, which has been found in some biologically active molecules, is presented as a demonstration of the synthetic utility of this method. Dependent on its other half: The title reaction of ortho-alkynylaryl ketones in the presence of a silver catalyst with a chiral counteranion afforded 1H-isochromene derivatives in high yield with good to high enantioselectivity (see scheme; R1=alkyl, aryl; R2=aryl; R3=H, F). An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6- diene framework found in biologically active molecules highlights the synthetic utility of this method. Copyright
- Terada, Masahiro,Li, Feng,Toda, Yasunori
-
supporting information
p. 235 - 239
(2014/01/17)
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- One-pot transition-metal-free synthesis of weinreb amides directly from carboxylic acids
-
Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.
- Niu, Teng,Wang, Ke-Hu,Huang, Danfeng,Xu, Changming,Su, Yingpeng,Hu, Yulai,Fu, Ying
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p. 320 - 330
(2014/02/14)
-
- Versatile synthesis of acylfuranones by reaction of acylketenes with α-hydroxy ketones: Application to the one-step multicomponent synthesis of cadiolide B and its analogues
-
Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues. A new method for the synthesis of acylfuranones is described based on the fragmentation of dioxinones to acylketenes followed by trapping with hydroxy ketones. Addition of an aldehyde as a third reaction partner leads to a supplementary aldolization/crotonization sequence resulting in an expeditious synthesis of cadiolide B and its analogues. Copyright
- Peixoto, Philippe Alexandre,Boulange, Agathe,Leleu, Stephane,Franck, Xavier
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p. 3316 - 3327
(2013/06/27)
-
- Synthesis of functionalised 4H-quinolizin-4-ones via tandem Horner-Wadsworth-Emmons olefination/cyclisation
-
4H-Quinolizin-4-ones are a unique class of heterocycle with valuable physicochemical properties and which are emerging as key pharmacophores for a range of biological targets. A tandem Horner-Wadsworth-Emmons olefination/cyclisation method has been developed to allow facile access to substituted 4H-quinolizin-4-ones encoded with a range of functional groups.
- Muir, Calum W.,Kennedy, Alan R.,Redmond, Joanna M.,Watson, Allan J. B.
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supporting information
p. 3337 - 3340
(2013/06/05)
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- Highly efficient and environmentally benign preparation of Weinreb amides in the biphasic system 2-MeTHF/water
-
A straightforward chromatography-free preparation of Weinreb amides starting from acid halides has been achieved in the biphasic medium 2-MeTHF/water. Analytically pure compounds were isolated in excellent yields simply after removal of 2-MeTHF, which abs
- Pace, Vittorio,Castoldi, Laura,Alcantara, Andres R.,Holzer, Wolfgang
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p. 10158 - 10162
(2013/09/02)
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- Facile preparation of amides from carboxylic acids and amines with ion-supported Ph3P
-
Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide (IS-Ph3P), could be used for the facile amidation of a wide range of carboxylic acids with amines in the presence of bromotrichloromethane to provide the corresponding amides in good yields. In the present reaction, the desired amides were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether or chloroform and subsequent removal of the solvent from the extract. Moreover, ion-supported Ph3PO (IS-Ph3PO), which was a co-product derived from IS-Ph3P in the present reductive condensation, was recovered in high yield and could be reduced to IS-Ph3P for reuse in the same amidation of carboxylic acid.
- Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
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p. 3971 - 3977
(2013/06/27)
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- The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction
-
A highly efficient carboxylate-phosphate anhydride pathway is described for the direct, economical synthesis of esters and amides from carboxylic acids and alcohols or amines. The reaction proceeds with retention of configuration with both chiral secondary alcohols and α-amino acid derivatives allowing access to useful chiral auxiliaries, ligands, and organocatalysts. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.
- McNulty, James,Vemula, Ramesh,Krishnamoorthy, Venkatesan,Robertson, Al
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experimental part
p. 5415 - 5421
(2012/09/08)
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- Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents
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KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives wit
- Hayashi, Yoshio,Yamazaki, Yuri,Sumikura, Makiko,Masuda, Yurika,Hayashi, Yoshiki,Yasui, Hiroyuki,Kiso, Yoshiaki,Chinen, Takumi,Usui, Takeo,Yakushiji, Fumika,Potts, Barbara,Neuteboom, Saskia,Palladino, Michael,Lloyd, George Kenneth
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experimental part
p. 4279 - 4289
(2012/09/08)
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- A Weinreb amide approach to the synthesis of trifluoromethylketones
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A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.
- Rudzinski, Diandra M.,Kelly, Christopher B.,Leadbeater, Nicholas E.
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supporting information
p. 9610 - 9612
(2012/10/29)
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- Ru-catalyzed hydrogenation of 3,5-diketo amides: Simultaneous control of chemo- and enantioselectivity
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By modulating the chelating priorities of the different directing groups in 3,5-diketo amides with the assistance from coordinating solvent, highly chemo- and enantioselective hydrogenation of the C3-carbonyls was achieved in the presence of [RuCl(benzene)(S)-SunPhos]Cl in THF.
- Li, Wanfang,Fan, Weizheng,Ma, Xin,Tao, Xiaoming,Li, Xiaoming,Xie, Xiaomin,Zhang, Zhaoguo
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supporting information
p. 8976 - 8978
(2012/11/07)
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- Microwave-assisted synthesis of weinreb and MAP aryl amides via pd-catalyzed heck aminocarbonylation using Mo(CO)6 or W(CO) 6
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A simple and expedient process for the Heck aminocarbonylative synthesis of Weinreb and MAP amide acylating agents, from aryl halides, is reported. This methodology utilizes solid sources of CO making it readily accessible to chemists working in small-scale laboratory applications.
- Wieckowska, Anna,Fransson, Rebecca,Odell, Luke R.,Larhed, Mats
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supporting information; experimental part
p. 978 - 981
(2011/03/22)
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- SUBSTITUTED PYRROLES AND IMIDAZOLES AS ESTROGEN RECEPTOR LIGANDS
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The invention provides a compound of formula (I) wherein G is a pyrrole or imidazole moiety and R4, R5, R6, R7 are as defined in the specification; or a pharmaceutically acceptable ester, amide, solvate or salt thereof, including a salt of such an ester or amide, and a solvate of such an ester, amide or salt. The invention also provides the use of such compounds in the treatment or prophylaxis of a condition associated with a disease or disorder associated with estrogen receptor activity.
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Page/Page column 40; 41
(2011/04/26)
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- Palladium-catalyzed preparation of Weinreb amides from boronic acids and N-methyl-N-methoxycarbamoyl chloride
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(Chemical Equation Presented) A simple protocol for the synthesis of Weinreb benzamides and α,β-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates. 2010 American Chemical Society.
- Krishnamoorthy, Ravi,Lam, Sang Q.,Manley, Christopher M.,Herr, R. Jason
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supporting information; experimental part
p. 1251 - 1258
(2010/04/29)
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- Poly(vinyl ketone)s by controlled boron group transfer polymerization (BGTP)
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(Figure Presented) Boron can do it! Readily prepared catecholboron enolates act as regulators in the controlled radical polymerization of alkyl and aryl vinyl ketones. Control is achieved by an unprecedented reversible radical boron group transfer (BGT) between enoyl radicals (see scheme). Polymers with M n-1 and a polydispersity index of 1.3 can be obtained by this process.
- Uehara, Kazuhiro,Wagner, Christine B.,Vogler, Thomas,Luftmann, Heinrich,Studer, Armido
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supporting information; experimental part
p. 3073 - 3076
(2010/07/05)
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- A halide-initiated aza-Baylis-Hillman reaction: Generation of unnatural amino acids
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A series of allenic ketones react with a glyoxylate-derived imine in the presence of MgBr2 through an aza-Morita-Baylis-Hillman (MBH) reaction. The isolation of a variety of unnatural amino acids with unique allene-containing functional groups
- Davis, Lindsey O.,Tobey, Suzanne L.
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supporting information; experimental part
p. 6078 - 6081
(2011/01/04)
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