A5100435170- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Radical Photochemical Reactions
- Phosphorus compounds and reactions
- Sulfur-Based Synthesis Techniques
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Catalytic Alkyne Reactions
- Gene expression and cancer classification
- Fluorine in Organic Chemistry
- Chemical Synthesis and Reactions
- Click Chemistry and Applications
- Organophosphorus compounds synthesis
- Synthesis and Catalytic Reactions
- Advanced Synthetic Organic Chemistry
- Alkaloids: synthesis and pharmacology
- Genomic variations and chromosomal abnormalities
- Nanoparticle-Based Drug Delivery
- Synthesis and pharmacology of benzodiazepine derivatives
- Photopolymerization techniques and applications
- Water Quality Monitoring and Analysis
- Synthesis of Organic Compounds
Nanjing Forestry University
2022-2025
University of California, Los Angeles
2014-2019
University of California System
2014-2018
Los Angeles City College
2018
Xinjiang University
2016
Tianjin University of Technology
2015
Nankai University
2010
Tianjin University
2005
University of Alabama at Birmingham
2004
Max Planck Institute for Plasma Physics - Greifswald
2002
Described herein is a catalytic asymmetric total synthesis of (-)-actinophyllic acid, with the key step being chiral phosphine-catalyzed [3 + 2] annulation between an imine and allenoate to form pyrroline intermediate in 99% yield 94% ee. The also features CuI-catalyzed coupling ketoester 2-iodoindole shape tetrahydroazocine ring; intramolecular alkylative lactonization; SmI2-mediated pinacol ketone lactone subunits assemble complex skeleton acid; unprecedented regioselective dehydroxylation.
Many natural products and medicinal drugs are heterocyclic amines possessing a chiral quaternary carbon atom in their ring. Herein, we report the first catalytic asymmetric Staudinger–aza-Wittig reaction for desymmetrization of ketones. This highly enantioselective transformation proceeds at room temperature to provide high yields—even on multigram scales—of nitrogen heterocycles featuring center. The this potential precursors synthesis pharmaceuticals. A commercially available small...
Abstract Alcohols are ubiquitous in chemistry and native functionalities many natural products bioactive molecules. As such, a strategy that utilizes hydroxy-containing compounds to develop bond disconnection formation process would achieve molecular diversity. Herein we utilize bench-stable N -alkoxyphthalimides prepared from alcohols couple with glycine derivatives via radical under visible light irradiation, providing variety of unnatural amino acid (UAA) peptide derivatives. The approach...
A bridged [2.2.1] bicyclic phosphine oxide has been created and applied successfully in halide-/base-free catalytic γ-umpolung addition–Wittig olefinations.
Herein, we disclose a Rh(III)-catalyzed C–H activation/annulation reaction for the derivatization of Lys-based peptides, in situ affording diverse peptide-isoquinolone conjugates. This approach features racemization-free conditions, high atom- and step-economy, excellent chemo- site-selectivity, broad scope including substrates bearing unprotected Trp Tyr, free Ser Gln, Met residues. The conjugates also display good fluorescent properties with maximum emission wavelengths up to 460 nm....
A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted presence of PPh2Et, naphthalene derivatives also obtained up to quantitative The mechanism latter transformation is straightforward: aldol addition followed by Wittig olefination dehydration. former a tandem...
A novel phosphine-catalyzed intermolecular cyclization between 2-sulfonamidobenzaldehyes and ynones is reported. This methodology serves as a conduit for the construction of benzo[b]azepin-3-ones in good to excellent yields under mild conditions. The resulting 2-benzylidene moieties are formed exclusively E-configuration. Mechanistically, this unusual annulation occurs through α-umpolung addition, followed by an aldol reaction. One benzo[b]azepin-3-one products was converted core structure...
The alkylation of nitro compounds is an efficient technique to augment molecular complexity, as exemplified by the Henry reaction and Michael addition involving sp2-hybridized carbon. However, a challenge arises in with sp3-hybridized carbon due competing nonproductive O-alkylation. In this study, we have developed manganese-promoted oxidative nitroalkanes using cyclopropyl alcohols via solvent-caged free-radical nucleophilic substitution pathway. This process yields variety γ-nitroketones,...
Abstract Photocatalytic generation of alkoxy radicals is fast emerging as an essential method for the diverse and valuable from inert C−H C−C bonds construction various C(sp 3 )−C(sp ), 2 )−C(sp), C−heteroatom under mild condition. This review a comprehensive evaluation studies using N‐ alkoxyphthalimide (NAPI) derivatives tunable oxygen radical precursors in photoredox catalysis, highlighting enabled 1,2‐, 1,5‐hydrogen atom transfer, β ‐fragmentation (deformylation) process to generate...
A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, reaction involves a Michael addition an alkylideneazinate rearrangement cyclic nitronate α-nitrosodihydrofuran.
A DABCO catalyzed domino reaction between 3-oxo-4-(2-oxoindolin-3-ylidene) butanoates and allenoates furnished 2,3,5-substituted tetrahydrofuran furan derivatives bearing oxindole moiety two exocyclic double bonds in high yield.
Abstract An important goal of modern synthetic chemistry is the development highly efficient and selective processes that minimize formation waste, which are desirable for economy environmental requirements. The classic Mitsunobu reaction has been adopted widely converting alcohols into numerous functional groups undergoes an inversion stereochemistry in S N 2 when secondary employed. However, far from ideal terms its impact, requiring stoichiometric amounts a phosphine (III)...
A C6' bulky substituted quinine-catalyzed SNV reaction between 3-substituted oxindole and (E)-3-(nitromethylene)-oxindole was developed. This enantioselective C(sp3)-C(sp2) coupling furnished bisoxindole scaffolds featuring a vinyl-substituted all-carbon quaternary stereocenter with high stereoselectivities. In addition, the gram-scale synthesis synthetic post-transformations were conducted to demonstrate potential usefulness.
Promising in vitro antifungal activity was demonstrated by the hydrazine and 4,5-dihydropyrazole core structures.
Abstract A catalyst‐free domino reaction was developed for the synthesis of 3‐(cyclopentenone)oxindoles. This method is first example a phosphine‐ylide‐initiated Wittig/Michael addition/Wittig sequence. The mild conditions and broad functional groups tolerance make it highly valuable synthesizing
Methods for the synthesis of chiral organic compounds bearing pyridyl-substituted stereogenic centers are great interest to agrochemical, pharmaceutical, and synthetic laboratories in their search unique entities. Here, a concise modular method enantioconvergent hydroalkylation widely available alkenes introduce C(sp3) has been established via nickel/Box catalyst with α-pyridyl alkyl bromide. The mild reaction conditions enable remarkably broad substrate scope good functional-group...
Abstract During the past decades, a variety of routes for total synthesis camptothecin have been reported. Considering only ( S )‐camptothecin and analogues possessing ability to inhibit DNA enzyme topoisomerase I, numerous advances achieved asymmetric camptothecin, providing concise scalable approaches academic community pharmaceutical industry. This review outlines recent in is timely highly desirable rapid development this field. By constructing chiral tertiary alcohol center, diverse...
Alcohols are the most commercially abundant, synthetically versatile and operationally convenient functional groups in organic chemistry. Therefore, a strategy that utilizes hydroxy-containing compounds to develop novel bond disconnection formation process would achieve molecular diversity. Herein, deconstructive for generation of quinoxalin-2(1H)-one derivatives has been developed from alcohol precursors via oxy-radical-induced β-fragmentation. Additionally, 1,5-HAT deoxygenation by P(III)...
A straightforward method for the phosphorylation of electron-deficient alkenes and aryl alkynes has been developed, leading to C(sp