Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
An efficient method for the asymmetric synthesis of 4H-3,1-benzoxazines was developed by kinetic resolution of 2-amido benzyl alcohols using chiral phosphoric acid catalyzed intramolecular cyclizations. A broad range of benzyl alcohols (both secondary and tertiary alcohols) were kinetically resolved with high selectivities, with an s factor of up to 94. Mechanistic studies were performed to elucidate the mechanism of these reactions, wherein the amide moieties reacted as the electrophiles. Gram-scale reaction and facile transformations of the chiral products demonstrate the potential of this method in asymmetric synthesis of biologically active chiral heterocycles.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201913896 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Ru-amidobis(phosphine) catalyzed alkylation of indole and epoxide opening followed by α-alkylation through alcohol oxidation.
Org Biomol Chem
September 2025
Phosphorus Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Herein, we report a simple, microwave-assisted and open-air strategy for gram-scale C3-alkylation of indoles, along with an economically viable strategy for epoxide opening followed by α-alkylation, using the [RuCl(bpy){-PhPCHCONCHPPh-}-κ-(,,,,)] complex (hereafter referred to as [PNP-Ru]). This transformation proceeds an alcohol dehydrogenation (oxidation) mechanism, with water being the sole byproduct in both reactions, underscoring the environmentally benign and sustainable nature of the methodology. The protocol efficiently delivers both mono- and bis(indolyl) derivatives in good to excellent yields.
View Article and Find Full Text PDFV NMR Spectroscopy and Ring-Size Effects on Catalytic Oxidative Alcohol Dehydrogenation in {V(O)(μ-O)(pin)} Oligomers.
Inorg Chem
September 2025
Boston University, Chemistry Department, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
Previously published (NMe)[V(O)(μ-O)(pin)], has been shown to aerobically catalyze the oxidation of benzylic and allylic alcohols under mild conditions. Herein, we report syntheses of [V(O)(μ-O)(pin)] trimers, which are also active in OAD catalysis. Trimer formation requires an ammonium cation with at least two hydrogen atoms per cation (e.
View Article and Find Full Text PDFInvestigating the mechanism of gastrodin-regulated miR-128-3p in methamphetamine dependence via integrated pharmacology.
Medicine (Baltimore)
September 2025
Department of Pharmacology of Chinese Medicine, School of Traditional Chinese Medicine, Southern Medical University, Guangzhou, China.
Gastrodin (GAS), the principal bioactive component derived from Gastrodia elata Bl., has demonstrated efficacy in attenuating methamphetamine (MA) induced conditioned place preference (CPP) in animal models. However, the molecular mechanisms underlying its anti-addictive effects, particularly the role of miRNAs, remain insufficiently understood.
View Article and Find Full Text PDFThree-Step One-Pot Photocatalytic Oxidation of Feedstocks and Organocatalytic Sequential Cascade to Access Enantioenriched α-Aminonitriles.
ChemSusChem
September 2025
Organic Chemistry Institute, University of Münster, Corrensstraße 36, 48149, Münster, Germany.
A three-step, one-pot, sequential cascade starting from simple feedstocks to increase complexity toward value-added chiral synthetic building blocks is reported. This is achieved by precisely integrating organic photocatalysis and noncovalent organocatalysis, often operating at dissimilar conditions and reaction media. In particular, this strategy is used to enable the direct transformation of readily available benzylic substrates, such as methylbenzenes, benzyl alcohols, or amines, into enantioenriched α-aminonitriles by benzylic CH photooxidation to their corresponding aldehydes, followed by in situ imine formation and final asymmetric organocatalytic Strecker reaction.
View Article and Find Full Text PDFEster-Aroyl-S,N-Ketene Acetals with Solid-State Luminescence: AIEgens from Sequential Three-Component Desymmetrization.
Chemistry
September 2025
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225, Düsseldorf, Germany.
Di(hetero)aroyl dichlorides are desymmetrized upon sequential reaction with alcohols and 2-methyl N-benzyl thiazolium salts within the course of a one-pot three-component reaction yielding ester-substituted aroyl-S,N-ketene acetals under mild conditions in good yields. A prerequisite for the concise one-pot process is the different nucleophilicity of the alcohols and in situ generated S,N-ketene acetals. The resulting compounds are merocyanines with dominant charge-transfer absorption bands which are fluorescent in the solid state, but not in solution.
View Article and Find Full Text PDF