Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ja00823a042 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electrochemical Dicarboxylation of Vinyl Epoxide with CO for the Facile and Selective Synthesis of Diacids.
Angew Chem Int Ed Engl
December 2024
State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.
We present a novel electrochemical dicarboxylation of epoxides with CO, characterized by the cleavage of two C-O single bonds. Not only are vinyl epoxides viable, but cyclic carbonates also serve as effective substrates, facilitating the synthesis of E-configured adipic and octanedioic acids with high chemo-, regio-, and stereoselectivity. The synthetic practicality is further highlighted by the diverse functionalizations of the resulting multifunctional diacids.
View Article and Find Full Text PDFNontraditional Synthesis of Disaccharides via Acyclic Vinylic Ether Intermediates: Catalytic C-O Cross-Coupling as the Enabling Link.
J Org Chem
December 2024
Department of Chemistry, Emory University, 1515 Dickey Drive NE, Atlanta, Georgia 30322, United States.
We describe complementary methods for synthesizing acyclic vinylic ethers from two carbohydrate-derived synthons. We compare a nonstereoselective olefination approach with a stereoselective catalytic C-O cross-coupling method, preparing 1,2-disubstituted vinylic ethers with complexity on both sides of the ether linkage. Upon epoxidation/ oxacyclization of acyclic vinylic ethers, we synthesized disaccharides with α-d-galacto-, α-d-talo-, β-d-allo-, and α-d-altropyranoside stereochemistry, from d-lyxose and d-ribose precursors.
View Article and Find Full Text PDFAminodiols, aminotetraols and 1,2,3-triazoles based on -gibberic acid: stereoselective syntheses and antiproliferative activities.
RSC Adv
November 2024
Institute of Pharmaceutical Chemistry, Interdisciplinary Excellent Center, University of Szeged Eötvös utca 6 H-6720 Szeged Hungary +36-62-545705 +36-62-546809.
A new series of aminodiols, aminotetraols and 1,2,3-triazoles based on -gibberic acid were synthesized in a stereoselective manner, starting from commercially available gibberellic acid. -Gibberic acid, prepared from gibberellic acid according to a literature method, was applied to SeO/-BuOOH-mediated allylic oxidation, yielding the triol, which is a key intermediate. After protecting the 1,4-diol functionality as acetonide, epoxidation was performed using either -CPBA or -BuOOH/VO(acac) to produce the epoxy alcohol.
View Article and Find Full Text PDFSkeletal Isomerization of Ergosterol-5,8-Peroxide Leading to the Discovery of Unprecedented Ergostanes and Collective Syntheses of 5,6-Epoxysterols and (+)-Sarocladione.
Chemistry
January 2025
Department of Applied Chemistry, Faculty of Engineering and Graduate School of Engineering, Osaka Institute of Technology, 5-16-1 Omiya, Asahi-ku, Osaka, 535-8585, Japan.
Skeletal isomerization of ergosterol peroxide, a primary oxidation product of ergosterol, was investigated under thermal and iron(II)-mediated conditions. Thermal isomerization resulted in not only the isolation of the predicted 7-hydroxy-5,6-epoxides but also the discovery of the unprecedented 7/9/5-ring-fused ergostane for the first time. The iron(II)-mediated isomerization proceeded at ambient temperature, resulting in the formation of the expected 5,6-epoxysterols and a ring-opened bicyclic diketone.
View Article and Find Full Text PDFComputational design for enantioselective CO capture: asymmetric frustrated Lewis pairs in epoxide transformations.
Beilstein J Org Chem
October 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Carbon capture and utilisation (CCU) technologies offer a compelling strategy to mitigate rising atmospheric carbon dioxide levels. Despite extensive research on the CO insertion into epoxides to form cyclic carbonates, the stereochemical implications of this reaction have been largely overlooked, despite the prevalence of racemic epoxide solutions. This study introduces an in silico approach to design asymmetric frustrated Lewis pairs (FLPs) aimed at controlling reaction stereochemistry.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!