Conjugate addition reactions of aldehydes to nitroolefins provide synthetically useful gamma-nitroaldehydes. Here we summarize our research on peptide-catalyzed conjugate addition reactions of aldehydes to differently substituted nitroolefins. We show that peptides of the general type Pro-Pro-Xaa (Xaa = acidic amino acid) are not only highly active, robust and stereoselective catalysts but have also remarkable chemoselectivities.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.2533/chimia.2013.279 | DOI Listing |
Inorg Chem
January 2025
Testing and Analysis Center, Hebei Normal University, Shijiazhuang 050024, China.
The bipyridyl tantalum complex (2,6-PrCHO)Ta(bipy) () is synthesized by the reaction of (2,6-PrCHO)TaCl () and 2,2'-bipyridine in the presence of excess potassium graphite (KC). Complex coordinates readily with pyridine and 4-(dimethylamino)pyridine (dmap) to form Lewis base adducts (2,6-PrCHO)Ta(bipy)(L) (L = py (), dmap ()), and it exhibits rich redox reactivity toward small molecules: (a) single electron transfer (SET) occurs upon exposure of to phenyl sulfide or selenide dimer, giving the open-shell, bipy-centered radical complexes (2,6-PrCHO)Ta(bipy)(PhE) (E = S (), Se ()). (b) Regioselective C-C σ-bond formation via radical coupling is observed in the SET reaction of and aldehydes, ketones, or imines to furnish insertion products -, namely, sterically more crowded benzophenone, acetophenone, 2,6-dichlorobenzaldehyde, and benzophenone imine couple with C6 or C6' of bipy in , respectively, whereas sterically less hindered benzaldehyde, cyclohexanone, and benzylideneaniline couple with C2 or C2' of bipy, respectively.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
IISER Kolkata: Indian Institute of Science Education and Research Kolkata, Department of Chemical Sciences, Mohanpur, 741246, Nadia, INDIA.
Chiral allyl amines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allyl amines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFACS Catal
January 2025
Molecular Sciences Research Hub, Imperial College London, 82 Wood Lane, Shepherds Bush, London W12 0BZ, U.K.
Aryl aldehydes are key synthetic intermediates in the manufacturing of active pharmaceutical ingredients. They are generated on scale (>1000 kg) through the palladium-catalyzed formylation of aryl bromides using syngas (CO/H). The best-in-class catalyst system for this reaction employs di-1-adamantyl--butylphosphine (cataium A), palladium(II) acetate, and tetramethylethylenediamine.
View Article and Find Full Text PDFR Soc Open Sci
January 2025
Department of Chemistry, SAS, Vellore Institute of Technology, Chennai, Tamil Nadu 600127, India.
Oxidation reactions are vital tools in synthetic organic chemistry. Oxidation of organic species such as alcohols, phenols, aldehydes and ketones provides synthetically valuable organic compounds, especially synthetic intermediates for several biologically active compounds. Some of these synthetic intermediates have shown their synthetic utility in the total synthesis of natural products.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!