An asymmetric allylic dearomatization reaction of 1-nitro-2-naphthol derivatives with Morita-Baylis-Hillman (MBH) adducts has been developed. By utilizing Pd catalyst derived from Pd(OAc) and Trost ligand (,)-L1, the reaction proceeded smoothly in 1,4-dioxane at room temperature, affording substituted β-naphthalenones in good yields (up to 92%) and enantioselectivity (up to 90% ee). A range of substituted 1-nitro-2-naphthols and MBH adducts were found to be compatible under the optimized conditions. This reaction provides a convenient method for the synthesis of enantioenriched 1-nitro-β-naphthalenone derivatives.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d3cc00568b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Axially Chiral Phenanthroline Ligand-Enabled Pd-Catalyzed Asymmetric Amination and Alkylation of Aryl-Substituted Morita-Baylis-Hillman Adducts.
Org Lett
December 2024
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
Highly enantioselective allylic amination and alkylation of racemic sterically hindered aryl-substituted Morita-Baylis-Hillman (MBH) adducts have been achieved by using an in situ formed Pd-catalyst from an axially chiral phenanthroline ligand. This dynamic kinetic asymmetric transformation (DYKAT) is compatible with cyclic and acyclic secondary amines, dialkyl malonates, β-keto esters, acetylacetone, and malononitrile, affording the corresponding chiral products, such as β-amino acid esters, in up to 95% yield and with up to a 99:1 enantiomeric ratio.
View Article and Find Full Text PDFA Regioselective, One-Pot, Transition-Metal-Free α-Alkylation of Quinone Monoacetals for Various Organic Transformations.
Org Lett
November 2024
Department of Chemistry, Indian Institute of Technology Delhi, New Delhi 110016, India.
Regioselective reactions of biologically significant quinones are challenging. An unprecedented advancement in quinone monoacetal (QMA) chemistry is proposed for constructing regioselective and less explored α-alkylated QMAs through the Morita-Baylis-Hillman (MBH) reaction. Electrophilic QMAs were transformed to nucleophilic umpolung reagents for aldol-type condensation with several electrophiles.
View Article and Find Full Text PDFDomino Sequence of Ketimization and Electrophilic Amination for an Inverse Aza Intramolecular Morita-Baylis-Hillman Adduct.
J Org Chem
October 2024
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
Morita-Baylis-Hillman (MBH) reaction, typically catalyzed by a Lewis base, is a popular and useful method for C-C bond formation. Unfortunately, it is limited by a slow reaction rate and has sensitivity toward steric and electronic parameters. Despite tremendous efforts, the versatility of the reaction keeps the quest open for new mechanistic and catalytic pathways.
View Article and Find Full Text PDFRegioselective Oxidation of Tetrahydronaphthalenes to α-Tetralone Derivatives Using DDQ as Oxidizing Agent: Synthesis and Evaluation of Antibacterial and Antifungal Activities.
ACS Omega
September 2024
Laboratory of Microorganisms and Active Biomolecules, LR03ES03, Department of Biology, Facultyof Sciences of Tunis, University of Tunis-El Manar, 2092 Tunis, Tunisia.
An easy and efficient approach for the synthesis of highly regioselective functionalized dihydronaphthalen-1(2)-one family of α-tetralones from functionalized tetralone precursors which derived from Morita-Baylis-Hillman (MBH) adducts as starting substrates has been developed. The target dihydronaphthalen-1(2)-ones are obtained through the oxidation of tetrahydronaphthalenes (THN) using DDQ as the oxidizing agent, conducted in aqueous acetic acid at reflux conditions. The yields obtained ranged from 90 to 98%.
View Article and Find Full Text PDFSynthesis and molecular docking analysis of MBH adducts' derived amides as potential inhibitors.
Bioinformation
May 2024
Center of Excellence in Genomic Medicine Research, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
Humans suffer from various diseases that require more specific drugs to target them. Among the different potent agents, s serve as good antibacterial agents; however, s are resistant to such antibiotics. The present study was designed to prepare efficient inhibitor amides (12-15) from inexpensive, easily accessible, and bioactive precursors; Morita Baylis Hillman (MBH) adducts (5-8).
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!