An intermolecular Pd-catalyzed allylic dearomatization reaction of polycyclic indoles with substituted allylic carbonates was realized in the presence of a newly synthesized chiral phosphoramidite ligand. Various polycyclic indoline and indolenine derivatives were successfully synthesized in excellent yields (up to 99%) with excellent enantioselectivity (up to 98% ee). The obtained products could undergo versatile transformations, increasing the application potential of the method in organic synthesis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b03887 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Organocatalytic Stereodivergent Dearomatization and -Acylation of 2-Amino-3-subsituted Indoles.
Org Lett
December 2024
Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology Guangming Advanced Research Institute, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China.
Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With BocO as reaction partner, the organocatalytic enantioselective -acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22-98% yields with 73-92% ee.
View Article and Find Full Text PDFIridium/Acid-Dual Catalyzed Enantioselective Intramolecular Allylic Dearomatization Reaction of Allylic Alcohol Tethered α- and β-Naphthols.
Chemistry
November 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Assam, 781039, India.
The first catalytic enantioselective intramolecular allylic dearomatization of allylic alcohol tethered α- and β-naphthols has been developed with iridium/acid-dual catalysis. A wide range of polycyclic spiroketones containing vicinal tertiary and quaternary carbon stereocenters were readily prepared in good to high yields with high diastereo- and moderate to excellent enantioselectivities. An unusual anti-Markovnikov Wacker oxidation has also been shown in synthetic transformations.
View Article and Find Full Text PDFSynthetic Modification and Insecticidal Activity of 4--cis-Dihydroagarofuran Derivatives.
J Agric Food Chem
July 2024
College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, P. R. China.
Article Synopsis
- A new method was developed to create a key part of dihydroagarofuran by using 6-methoxy-1-tetralone and performing dearomatization followed by Michael addition reactions.
- A total of 33 synthesized compounds were tested for their insecticidal properties, with one showing an LC value of 0.378 mg/mL, indicating a significant increase in effectiveness compared to the known compound Celangulin V.
- Research identified that modifications, like adding methyl groups at certain positions and using specific ether groups, enhanced the insecticidal activity, and further analysis using a 3D model helped in understanding the relationship between the compound's structure and its effectiveness.
Total Synthesis of (±)-Simonsol C.
J Org Chem
June 2024
School of Chemistry and Environment, National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, Yunnan Minzu University, Kunming 650504, China.
Total synthesis of simonsol C has been achieved, focusing on the postdearomatization transformations. Our methodology integrates an efficient combination of dearomatization and Zn/AcOH reduction to introduce an allyl group, followed by oxo-Michael addition, to construct the 6/5/6 benzofuran skeleton. It offers a novel method for synthesizing allyl-containing quaternary carbon atoms in a straightforward manner.
View Article and Find Full Text PDFStability and reactivity of alkylidene dihydropyridines.
Org Biomol Chem
May 2024
Department of Chemistry, York University, Toronto, ON, M3J 1P3, Canada.
Alkylidene dihydropyridines (ADHPs) are electron-rich nucleophilic intermediates that can be readily prepared by dearomatization of 4-alkylpyridines using chloroformate reagents and mild base. Their stability and reactivity can be tuned with the chloroformate reagent used as evidenced by NMR chemical shifts and oxidation potentials. ADHPs prepared with ethyl, allyl and trichloroethyl chloroformate undergo decomposition under an oxygen atmosphere at different rates (ethyl > allyl > trichloroethyl), predominantly to the corresponding 4-acylpyridine.
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!