A5015550210- Catalytic C–H Functionalization Methods
- Chemical Synthesis and Analysis
- Microbial Natural Products and Biosynthesis
- Oxidative Organic Chemistry Reactions
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Radical Photochemical Reactions
- Asymmetric Hydrogenation and Catalysis
- Alkaloids: synthesis and pharmacology
- Chemical Synthesis and Reactions
- Synthesis and Catalytic Reactions
- Advanced Synthetic Organic Chemistry
- Biochemical and Structural Characterization
- Crystallography and molecular interactions
- Axial and Atropisomeric Chirality Synthesis
Yale University
2024
Ben-Gurion University of the Negev
2015-2023
Abstract Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N ‐hydroxyphthalimide (NHPI) cobalt(II) acetate in 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), were developed. The sustainable enable a multigram scale preparation benzaldehyde derivatives high efficiency with excellent chemoselectivity (up 99 % conversion 98 selectivity).
Abstract Significant enhancement of both the rate and chemoselectivity iron‐catalyzed oxidative coupling phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), 1‐phenyl‐2,2,2‐trifluoroethanol. The generality this effect was examined for cross‐coupling with arenes polycyclic aromatic hydrocarbons (PAHs) phenol β‐dicarbonyl compounds. new conditions were utilized synthesis 2′′′‐dehydroxycalodenin B only four synthetic steps.
Methods to access chiral sulfur(VI) pharmacophores are of interest in medicinal and synthetic chemistry. We report the desymmetrization unprotected sulfonimidamides via asymmetric acylation with a cinchona-phosphinate catalyst. The desired products formed excellent yield enantioselectivity no observed bis-acylation. A data-science-driven approach substrate scope evaluation was coupled high throughput experimentation (HTE) facilitate statistical modeling order inform mechanistic studies....
Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged from amino acids. The approach was utilized preparing...
Abstract Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N ‐hydroxyphthalimide (NHPI) cobalt(II) acetate in 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), were developed. The sustainable enable a multigram scale preparation benzaldehyde derivatives high efficiency with excellent chemoselectivity (up 99 % conversion 98 selectivity).
The biosynthesis of glycopeptide antibiotics such as vancomycin and other biologically active biaryl-bridged diaryl ether-linked macrocyclic peptides includes key enzymatic oxidative phenol macrocyclization(s) linear precursors. However, a simple step-economical biomimetic version this transformation remains underdeveloped. Here, we report highly efficient conditions for preparing based on multicopper(II) clusters. selective syntheses ring models the arylomycin cyclic core illustrate...
Abstract Biaryl‐bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram‐negative bacteria. Herein, we present a simple, flexible, reliable strategy based on activating‐group‐assisted catalytic oxidative coupling for assembling biaryl‐bridged from amino acids. The approach was utilized...
In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which based on the FeCl3 catalyst t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with high degree of selectivity. generality conditions was proven by reacting various substituted phenols, naphthols, tyrosine 3-alkyloxindoles. To apply chemistry for conjugation tyrosine-containing short...
Methods to access chiral sulfur (VI) pharmacophores are of interest in medicinal and synthetic chemistry. We report the desymmetrization unprotected sulfonimidamides via asymmetric acylation with a cinchona-phosphinate catalyst. The desired products formed excellent yield enantioselectivity no observed bis-acylation. A data science-driven approach substrate scope evaluation was coupled high throughput experimentation (HTE) facilitate statistical modeling order inform mechanistic studies....
The biosynthesis of glycopeptide antibiotics such as vancomycin and other biologically active biaryl-bridged diaryl ether-linked macrocyclic peptides includes key enzymatic oxidative phenol macrocyclization(s) linear precursors. However, a simple step-economical biomimetic version this transformation remains underdeveloped. Here, we report highly efficient conditions for preparing based on multicopper(II) catalysts. selective syntheses ring models the arylomycin cyclic core illustrate...
Abstract Significant enhancement of both the rate and chemoselectivity iron‐catalyzed oxidative coupling phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), 1‐phenyl‐2,2,2‐trifluoroethanol. The generality this effect was examined for cross‐coupling with arenes polycyclic aromatic hydrocarbons (PAHs) phenol β‐dicarbonyl compounds. new conditions were utilized synthesis 2′′′‐dehydroxycalodenin B only four synthetic steps.
Abstract Phenols and naphthols are regioselectively coupled with 2‐oxocyclopentanoic acid ester (II), arenes (IV) (VII), polyaromatic hydrocarbons, e.
The biosynthesis of glycopeptide antibiotics such as vancomycin and other biologically active biaryl-bridged diaryl ether-linked macrocyclic peptides includes key enzymatic oxidative phenol macrocyclization(s) linear precursors. However, a simple step-economical biomimetic version this transformation remains underdeveloped. Here, we report highly efficient conditions for preparing based on multicopper(II) catalysts. selective syntheses ring models the arylomycin cyclic core illustrate...
In Figure 2 B of this Communication the CV curves were inappropriately assigned. corrected that can be found in Corrigendum, black curve belongs to Tyr 10, while red activated 11. The authors apologize for error. 2. A) HPLC chromatograms oxidative coupling compounds 10 and 11 by Fe[TPP]Cl (Table 1, entry 1). B) Cyclic voltammetry non-activated (black curve) (red curve). E(V) vs. Ag/0.01 m AgNO3.