30982-08-2Relevant articles and documents
Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins
White, Dawn H.,Noble, Adam,Booker-Milburn, Kevin I.,Aggarwal, Varinder K.
supporting information, p. 3038 - 3042 (2021/05/04)
A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.
Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines
Booker-Milburn, Kevin I.,Knowles, Jonathan P.,Latter, Francesca,Schwarz, Maria,Steeds, Hannah G.
supporting information, p. 4986 - 4990 (2021/07/19)
The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji-Trost sequence leading to a surprisingly facile intramolecular Diels-Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.
COMPOSITIONS AND METHODS FOR PROTEIN LABELING, MODIFICATION, ANALYSIS, AND TARGETED DELIVERY
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Paragraph 00224, (2020/01/24)
The invention relates to chemically reactive and/or biologically active compounds, reagents and compositions thereof. More particularly, the invention provides novel reagents that are useful in chemical synthesis, functionalization, delivery, probing and/or analytical measurements of small molecule drugs, proteins, antibodies and other biomolecules. The invention provides novel biologically active agents useful as diagnostics or therapeutics, and related composition and methods of uses thereof.
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
, (2020/10/02)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
The alkoxycarbonylation of protected propargyl alcohols
Alam, Md. Mahbubul,Beghetto, V.,Bertoldini, M.,Scrivanti, A.,Sole, R.
, (2020/09/02)
Palladium-catalyzed alkoxycarbonylation of the C≡C triple bond of propargyl alcohol is a sustainable synthetic approach to 2-(hydroxymethyl)acrylates, a family of valuable intermediates. The developed synthetic protocol includes protection of the alcoholic function of the alkyne before its carbonylation in the presence of Drent's catalytic system. Protection step effectively extends the catalyst life hence enhancing the practical applicability of the reaction. The effectiveness of some different protecting groups (benzyl, acetyl and trimethylsilyl) has been assessed and the influence of the reaction parameters investigated.
Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles
Katsina, Tania,Sharma, Sachi Prem,Buccafusca, Roberto,Quinn, Derek J.,Moody, Thomas S.,Arseniyadis, Stellios
supporting information, p. 9348 - 9352 (2019/11/20)
A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.
Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
Poklukar, Ga?per,Stephan, Michel,Mohar, Barbara
supporting information, p. 2566 - 2570 (2018/05/16)
A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).
Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids
Nascimento de Oliveira, Marllon,Arseniyadis, Stellios,Cossy, Janine
supporting information, p. 4810 - 4814 (2018/03/21)
We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2-amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.
Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation
Song, Tao,Arseniyadis, Stellios,Cossy, Janine
supporting information, p. 8076 - 8080 (2018/06/15)
The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.
ALPHA-(UNSATURATED ALKOXYALKYL) ACRYLATE COMPOSITION AND PROCESS FOR PRODUCTION THEREOF
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Page/Page column 63, (2012/02/15)
An α-(unsaturated alkoxyalkyl) acrylate composition is provided which enables an α-(unsaturated alkoxyalkyl) acrylate product to be stored at a high purity for an extended period of time and can fully suppress problems such as coloration and gelation from
