Pinacol coupling of alkyl dinitrones mediated by SmI2 was achieved in the presence of a proton source allowing the synthesis of cyclic vicinal diamines with good cis-selectivity.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b511491hDOI Listing

Publication Analysis

Top Keywords

pinacol coupling
8
synthesis cyclic
8
samarium diiodide-induced
4
diiodide-induced intramolecular
4
intramolecular pinacol
4
coupling dinitrones
4
dinitrones synthesis
4
cyclic cis-vicinal
4
cis-vicinal diamines
4
diamines pinacol
4

Similar Publications

Exploration of (R)-[C]YH168 as a PET tracer for imaging monoacylglycerol lipase in the brain: from mice to non-human primates.

Eur J Nucl Med Mol Imaging

December 2024

Center for Radiopharmaceutical Sciences, Institute of Pharmaceutical Sciences, Department of Chemistry and Applied Biosciences, ETH Zurich, Zurich, CH-8093, Switzerland.

Purpose: The monoacylglycerol lipase (MAGL) plays a pivotal role in modulating the endocannabinoid system and is considered an attractive therapeutic target for diseases in both the central nervous system and periphery. The current study aimed to develop and evaluate a suitable carbon-11 labeled tracer for imaging MAGL in preclinical studies.

Methods: (R)-YH168 was synthesized via a multi-step pathway and its half-maximal inhibitory concentration (IC) values were measured using an enzymatic assay.

View Article and Find Full Text PDF

Photochemical carboborylation and three-component difunctionalization of α,β-unsaturated ketones with boronic acids tosylhydrazones.

Chem Sci

November 2024

Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Instituto de Investigación Sanitaria del Principado de Asturias (ISPA), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo C/ Julián Clavería 8 33006 Oviedo Spain

The reactions of cyclic α,β-unsaturated -tosylhydrazones and alkylboronic acids promoted by 370-390 nm light in the presence of a base give rise to allylic boronic acids that can be trapped as the corresponding pinacolboronates by treatment with pinacol. This reaction features wide scope regarding both coupling partners and functional group tolerance, allowing for the incorporation of a variety of natural product-derived fragments. The allylic boronic acids can be also reacted in a one-pot process with aldehydes, to produce homoallylic alcohols with very high diastereoselectivity.

View Article and Find Full Text PDF

A two-step procedure, combining a SmI-mediated transannular pinacol coupling reaction with an acid-catalyzed pinacol rearrangement process, was employed to prepare a diverse range of 1-substituted bicyclo[2.1.1]hexan-5-ones from cyclobutanedione derivatives.

View Article and Find Full Text PDF

A Novel Anion Receptor Additive for -40 °C Sodium Metal Batteries by Anion/Cation Solvation Engineering.

Angew Chem Int Ed Engl

October 2024

College of Sciences/Institute for Sustainable Energy, Shanghai University, Shanghai, 200444, China.

Article Synopsis
  • * A new additive, 4-aminophenylboronic acid pinacol ester (ABAPE), helps improve sodium transport by reducing the interaction between anions and cations in the electrolyte, which leads to better battery performance.
  • * Adding ABAPE enhances the stability of the electrode-electrolyte interface and improves cycle life, resulting in a Na||NaV(PO) battery achieving an impressive 84.29% capacity retention after 1200 cycles and no capacity loss at -40°C over 150 cycles.
View Article and Find Full Text PDF

Enantioconvergent Cross-Nucleophile Coupling: Copper-Catalyzed Deborylative Cyanation.

Angew Chem Int Ed Engl

December 2024

Department of Chemistry, Colorado State University, 1301 Center Ave, Fort Collins, CO 80523-1872.

Organoboron compounds are widely utilized in organic synthesis for their diverse reactivity, modular preparation, and stability compared to other classes of organometallic reagents. While organoboron species are commonly employed as nucleophiles in cross-coupling reactions, their potential as racemic building blocks in enantioconvergent transformations remains largely untapped. Herein, we demonstrate the direct utilization of alkylboronic pinacol esters in intermolecular enantioconvergent transformations.

View Article and Find Full Text PDF

Want 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!