A synthetic approach to a new class of allyl nitro derivatives is reported. (2-Acetoxy)allyl nitro compounds have been prepared for the first time in a four-step procedure by a preliminary reaction of nitroalkanes with 2-(phenylselenyl)acetaldehyde. After the acetylation of the obtained nitro alcohols, the unsaturation is installed by an oxidation reaction involving the phenylselenyl group followed by a thermal elimination. The oxidation process is accomplished under flow conditions ensuring a notable lowering of overoxidation by products observed in batch.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b01744 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A scoping review of privacy and utility metrics in medical synthetic data.
NPJ Digit Med
January 2025
Biomedical Data Science Center, Centre Hospitalier Universitaire Vaudois, Lausanne, Switzerland.
The use of synthetic data is a promising solution to facilitate the sharing and reuse of health-related data beyond its initial collection while addressing privacy concerns. However, there is still no consensus on a standardized approach for systematically evaluating the privacy and utility of synthetic data, impeding its broader adoption. In this work, we present a comprehensive review and systematization of current methods for evaluating synthetic health-related data, focusing on both privacy and utility aspects.
View Article and Find Full Text PDFStrengthening biopolymer adhesives through ureolysis-induced calcium carbonate precipitation.
Sci Rep
January 2025
Department of Chemical & Biological Engineering, Montana State University, Bozeman, USA.
Common adhesives for nonstructural applications are manufactured using petrochemicals and synthetic solvents. These adhesives are associated with environmental and health concerns because of their release of volatile organic compounds (VOCs). Biopolymer adhesives are an attractive alternative because of lower VOC emissions, but their strength is often insufficient.
View Article and Find Full Text PDFFlow chemistry-enabled asymmetric synthesis of cyproterone acetate in a chemo-biocatalytic approach.
Nat Commun
January 2025
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, China.
Flow chemistry has many advantages over batch synthesis of organic small-molecules in terms of environmental compatibility, safety and synthetic efficiency when scale-up is considered. Herein, we report the 10-step chemo-biocatalytic continuous flow asymmetric synthesis of cyproterone acetate (4) in which 10 transformations are combined into a telescoped flow linear sequence from commercially available 4-androstene-3, 17-dione (11). This integrated one-flow synthesis features an engineered 3-ketosteroid-Δ-dehydrogenase (ReM2)-catalyzed Δ-dehydrogenation to form the C1, C2-double bond of A ring, a substrate-controlled Co-catalyzed Mukaiyama hydration of 9 to forge the crucial chiral C17α-OH group of D ring with excellent stereoselectivity, and a rapid flow Corey-Chaykovsky cyclopropanation of 7 to build the cyclopropyl core of A ring.
View Article and Find Full Text PDFAsymmetric Functionalization Harnessing Radical-Mediated Functional-Group Migration.
Angew Chem Int Ed Engl
January 2025
Shanghai Jiao Tong University, Frontiers Science Center for Transformative Molecules, 800 Dongchuan Road, 200240, Shanghai, CHINA.
Along with the renaissance of radical chemistry, the past decade has witnessed rapid development in radical-mediated rearrangement reactions. A wide diversity of radical approaches harnessing functional-group migration (FGM) have been devised to enhance both synthetic efficiency and molecular complexity. However, the application of FGM reactions to construct stereogenic centers remains underexplored owing to the inherent challenges of asymmetric radical reactions.
View Article and Find Full Text PDFEnhancing Electron Donor-Acceptor Complex Photoactivation with a Stable Perylene Diimide Metal-Organic Framework.
J Am Chem Soc
January 2025
Department of Chemistry, The University of Hong Kong, Hong Kong 999077, P. R. China.
Electron donor-acceptor complexes are commonly employed to facilitate photoinduced radical-mediated organic reactions. However, achieving these photochemical processes with catalytic amounts of donors or acceptors can be challenging, especially when aiming to reduce catalyst loadings. Herein, we have unveiled a framework-based heterogenization approach that significantly enhances the photoredox activity of perylene diimide species in radical addition reactions with alkyl silicates by promoting faster and more efficient electron donor-acceptor complex formation.
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!