- Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives
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Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.
- Sun, Xin,Bai, Xiao-Yan,Li, An-Zhen,Li, Bi-Jie
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supporting information
p. 2182 - 2187
(2021/03/01)
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- Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
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Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
- Gouverneur, Véronique,Hell, Sandrine M.,Laudadio, Gabriele,Meyer, Claudio F.,Misale, Antonio,No?l, Timothy,Trabanco, Andrés A.,Willis, Michael C.
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supporting information
p. 720 - 725
(2020/02/20)
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- COVALENT TARGETING OF E3 LIGASES
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Disclosed herein, inter alia, are compositions and methods for targeting E3 ligases. In an aspect is a targeted protein degrader including 1) a targeted protein binder and 2) an E3 Ubiquitin ligase binder, wherein the E3 Ubiquitin ligase is human RNF4 or human RNF114. In an aspect is provided a pharmaceutical composition including a compound as described herein, including embodiments, and a pharmaceutically acceptable excipient.
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Paragraph 0591; 0627
(2020/05/19)
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- Metal-Free C–S Bond Cleavage to Access N-Substituted Acrylamide and β-Aminopropanamide
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Metal-free and Selectfluor-mediated C–S bond cleavage is described. This novel strategy provides a facile and efficient method to access important N-substituted acrylamide and β-aminopropanamide derivatives with good functional group tolerance and yields.
- Yang, Ke,Li, Yi,Ma, Zhiyan,Tang, Long,Yin, Yue,Zhang, Hao,Li, Zhengyi,Sun, Xiaoqiang
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supporting information
p. 5812 - 5814
(2019/08/27)
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- Hindered amine antioxidant preparation method
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The invention discloses a hindered amine antioxidant preparation method, which comprises: (1) carrying out a substitution reaction on a halogenated aniline compound and an acyl halide compound to produce an intermediate (I); (2) carrying out a carbon-carb
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Paragraph 0044-0046; 0050; 0056; 0060; 0066; 0070
(2018/07/06)
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- Efficient cu-catalyzed atom transfer radical addition reactions of fluoroalkylsulfonyl chlorides with electron-deficient alkenes induced by visible light
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Fluoroalkylsulfonyl chlorides, RfSO2Cl, in which Rf=CF3, C4F9, CF2H, CH2F, and CH2CF3, are used as a source of fluorinated radicals to add fluoroalkyl groups to electron-deficient, unsaturated carbonyl compounds. Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process. Facile nucleophilic replacement of the α-chloro substituent is shown to lead to further diverse functionalization of the products.
- Tang, Xiao-Jun,Dolbier, William R.
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supporting information
p. 4246 - 4249
(2015/04/14)
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- Cascade synthesis of spirooxindole δ-lactone derivatives through N-aryl hydroxymethylacrylamides with xanthates
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A novel and highly efficient cascade synthesis of spirooxindole δ-lactone derivatives from N-aryl hydroxymethylacrylamides and xanthates in good yields is described. The reaction proceeds through a radical addition/cyclization and ester exchange, in which two new C-C bonds and one C-O bond were formed.
- Wang, Shucheng,Huang, Xuhu,Wen, Yanzhao,Ge, Zemei,Wang, Xin,Li, Runtao
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supporting information
p. 8117 - 8122
(2015/12/30)
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- Direct Photoredox-Catalyzed Reductive Difluoromethylation of Electron-Deficient Alkenes
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Photoredox-catalyzed reductive difluoromethylation of electron-deficient alkenes was achieved in one step under tin-free, mild and neutral conditions. This protocol affords a facile method to introduce RCF2 (R=H, Ph, Me, and CH2N3) groups at sites β to electron-withdrawing groups. It was found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H-atom donor and the electron donor in the catalytic cycle. Experimental and DFT computational results provided evidence that RCF2 (R=H, Ph, Me) radicals are nucleophilic in nature.
- Tang, Xiao-Jun,Zhang, Zuxiao,Dolbier, William R.
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supporting information
p. 18961 - 18965
(2016/01/26)
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- Ligand-free CuTC-catalyzed N-arylation of amides, anilines and 4-aminoantipyrine: Synthesis of N-arylacrylamides, 4-amido-N-phenylbenzamides and 4-amino(N-phenyl)antipyrenes
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N-Arylation of amides and anilines with aryl iodides was efficiently catalyzed by copper thiophenecarboxylate under ligand-free conditions with good to excellent yields. A variety of substituted aryl iodides, amides, anilines and 4-aminoantipyrine were found to be applicable to the simple catalytic system. Furthermore, some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, and 4-amino(N-phenyl)antipyrenes, which are difficult to obtain by the classical methods, were prepared.
- Quan, Zheng-Jun,Xia, Hai-Dong,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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- An efficient copper-catalyzed N-arylation of amides: Synthesis of N-arylacrylamides and 4-amido-N-phenylbenzamides
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Copper-catalyzed intermolecular C-N bond-forming reactions between aryl iodides and amides are described using sodium ascorbate, which is both cheap and nontoxic, as the additive. A variety of functionalized amides including some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, which are difficult to obtain by the classical methods, are prepared. Furthermore, some tertiary amides are prepared by using copper thiophenecarboxylate.
- Quan, Zheng-Jun,Xia, Hai-Dong,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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p. 8368 - 8374
(2013/09/02)
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- Discovery and structure-activity relationship of potent and selective covalent inhibitors of transglutaminase 2 for Huntington's disease
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Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.
- Prime, Michael E.,Andersen, Ole A.,Barker, John J.,Brooks, Mark A.,Cheng, Robert K. Y.,Toogood-Johnson, Ian,Courtney, Stephen M.,Brookfield, Frederick A.,Yarnold, Christopher J.,Marston, Richard W.,Johnson, Peter D.,Johnsen, Siw F.,Palfrey, Jordan J.,Vaidya, Darshan,Erfan, Sayeh,Ichihara, Osamu,Felicetti, Brunella,Palan, Shilpa,Pedret-Dunn, Anna,Schaertl, Sabine,Sternberger, Ina,Ebneth, Andreas,Scheel, Andreas,Winkler, Dirk,Toledo-Sherman, Leticia,Beconi, Maria,MacDonald, Douglas,Mu?oz-Sanjuan, Ignacio,Dominguez, Celia,Wityak, John
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p. 1021 - 1046
(2012/04/10)
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- Selenium-linking strategy for traceless solid-phase synthesis of acrylamides
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A novel polystyrene-supported β-selenopropionic acid has been developed and applied to simple and efficient synthesis of acrylamides.
- Sheng, Shou-Ri,Wang, Xing-Cong,Liu, Xiao-Ling,Song, Cai-Sheng
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p. 2867 - 2872
(2007/10/03)
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- A new route to N-aryl 2-alkenamides, N-allyl N-aryl 2-alkenamides, and N-aryl α,β-unsaturated γ-lactams from N-aryl 3-(phenylsulfonyl)propanamides
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A series of N-aryl 2-alkenamides were produced efficiently by treating N-aryl 3-(phenylsulfonyl)-propanamides with potassium tert-butoxide in THF at 0°C. Without isolation, it was further treated with an additional equivalent of potassium tert-butoxide and allyl bromide to give N-allyl N-aryl 2-alkenamides in one pot in good yields. Followed by a ring-closing metathesis reaction, these N-allyl N-aryl 2-alkenamides were respectively converted into corresponding N-aryl α,β-unsaturated γ-lactams in moderate yields.
- Wang, Eng-Chi,Huang, Keng-Shiang,Lin, Gwo-Woei,Lin, Jia-Ruei,Hsu, Ming-Kun
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