A5003467522- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Radical Photochemical Reactions
- Cyclopropane Reaction Mechanisms
- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Synthesis and Catalytic Reactions
- Asymmetric Hydrogenation and Catalysis
- Sulfur-Based Synthesis Techniques
- Fluorine in Organic Chemistry
- Oxidative Organic Chemistry Reactions
- Organic Chemistry Cycloaddition Reactions
- Computational Drug Discovery Methods
- Free Radicals and Antioxidants
- Synthetic Organic Chemistry Methods
- Ferrocene Chemistry and Applications
- Photochromic and Fluorescence Chemistry
- Polysaccharides and Plant Cell Walls
- Biomedical Text Mining and Ontologies
- Organoboron and organosilicon chemistry
- Organophosphorus compounds synthesis
- Catalysis for Biomass Conversion
- biodegradable polymer synthesis and properties
- Carbon dioxide utilization in catalysis
- Pneumocystis jirovecii pneumonia detection and treatment
University of Oxford
2021-2025
Max-Planck-Institut für Kohlenforschung
2019-2025
Oxford Research Group
2021-2022
Karlsruhe Institute of Technology
2021
Abstract Rigid 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) are linear bioisosteres for para -substituted benzene rings in drug development and can lead to an improved pharmacokinetic profile. The construction of BCPs commonly requires the cumbersome use labile [1.1.1]propellane solution, more stable reagents do not show versatile reactivity propellane itself. Here we report thianthrenium-based BCP practical O -, N - C -alkylation reactions that expand scope bicyclopentylation beyond any...
Prediction of the outcome ring opening small organic rings under cationic conditions can be challenging due to intermediacy nonclassical carbocations. For example, solvolysis cyclobutyl or cyclopropylmethyl derivatives generates up four products on nucleophilic capture elimination via cyclopropylcarbinyl and bicyclobutonium ions. Here, we show that such reaction outcomes controlled by subtle changes structure carbocation. Using bicyclo[1.1.0]butanes as cation precursors, regio-...
Bioderived furans play a pivotal role in advancing defossilized chemical pathways. The complete reduction of currently relies on impractical metal-catalyzed hydrogenations at high pressures and temperatures. In addition, the Birch unbiased to 2,5-dihydrofurans remains an unsolved synthetic challenge. Herein, we report mild Bro̷nsted acid-catalyzed 2,5-dihydro- and/or tetrahydrofuran derivatives using silanes as reducing agents. particular, first formal furan itself is achieved. Mechanistic...
We report a nucleophilic substitution reaction of five-membered hetarylsulfonium salts that results in change the pattern on arene. The products these cine-substitutions are hard to access synthetically otherwise. sulfonium serve as starting materials generated by highly site-selective C-H functionalization reaction.
The organophotocatalysed-generation of α-amino radicals enables the synthesis bicyclo[n.1.1]alkanes ( n = 1, 3) under mild conditions by addition to interbridgehead C–C bonds [n.1.1]propellanes.
Bicyclo[1.1.1]pentanes (BCPs) are important in drug design as sp3-rich bioisosteres of arenes and tert-butyl groups; however, the preparation BCPs with adjacent quaternary carbons is barely known. We report a facile synthesis α-quaternary using organophotoredox hydrogen atom transfer catalysis which α-keto radicals, generated through oxidation β-ketocarbonyls, undergo efficient addition to [1.1.1]propellane. The BCP products can be transformed into variety useful derivatives, including...
While naphthalene rings are often encountered in drugs, candidates and lead molecules, they can be susceptible to cy-tochrome P450-mediated metabolism biological systems exhibit flat, sp2-rich structures, limiting their utility drug-like candidates. Herein, we report the first library of derivatisable aryl-fused Bicyclo[3.1.1]heptanes (BCHeps) as bioisosteric replacements for (β-)naphthalene other fused bicyclic aromatics. We incorporate BCHep-based naphthyl isosteres into AhR antagonist...
The bioisosteric replacement of 2D aromatic scaffolds with sp3-rich surrogates has become an important design element in modern medicinal chemistry. Within the world, azabicyclo[2.1.1]hexane (aza-BCH) scaffold stands out as a pyrrolidine and useful building block. However, despite recent advancements field, modular enantioselective synthesis aza-BCHs remains challenging. In this study, we introduce asymmetric organocatalytic approach relying on confined imidodiphosphorimidate (IDPi) Brønsted...
Thiophene S,S-dioxides are underutilized tools for the de novo construction of benzene rings in organic synthesis. We report a collective synthesis nine illudalane sesquiterpenes using bicyclic thiophene as generalized precursors to indane core natural products. Exploiting furans unusual dienophiles this inverse electron demand Diels–Alder cascade, concise and convergent approach enables these targets little five steps. Theoretical studies rationalize reactivity with both electron-poor...
The positional selectivity of ring opening small, strained organic rings is often considered to be governed by the maximal release strain. However, reactions under cationic conditions can lead multiple products due intermediacy non-classical carbocations (carbonium ions cations featuring a formally pentavalent carbon atom). A famous example solvolysis cyclobutyl or cyclopropylmethyl derivatives, which proceed via two equilibrating cyclopropylcarbinyl ion (CC), and bicyclobutonium (BB)...
Abstract The synthesis and full characterization of novel 1,1′‐difunctionalized ferrocene metalloligands is described. While one cyclopentadienyl ring has been functionalized with 2,2′‐bipyridine for secondary coordination, the second Cp decorated different aryl moieties containing electron withdrawing groups such as 4‐(CF 3 )C 6 H 4 ( 2A ) 3,5‐(CF 2 C 2B or 4‐(NO 2C ). newly developed were reacted [Pd(cod)Cl ] 3A – ), CuCl 4A trans ‐[(PPh Ni(Mes)Br] 5A , B to obtain corresponding...
Small-ring cage hydrocarbons are common bioisosteres for para-substituted benzene rings in drug design, exhibiting superior pharmacokinetic properties compared to the parent aromatics. In contrast, scaffolds mimicking meta-substituted arenes lacking due challenge of synthesising saturated isosteres that accurately reproduce substituent vectors corresponding arene. Here we report use [3.1.1]propellane as a convenient and scalable precursor bicyclo[3.1.1]heptanes (BCHeps), whose bridgehead...
Ontologies order and interconnect knowledge of a certain field in formal semantic way so that they are machine-parsable. They try to define allwhere acceptable definition concepts objects, classify them, provide properties as well them with relations (e.g. "A is special case B"). More precisely, Tom Gruber defines "specification conceptualization; [...] description (like specification program) the relationships can exist for an agent or community agents." [1] An Ontology made Individuals...
Key words late-stage derivatization - amination arenes
Key words difluorination - hypervalent iodine difluorinated carbocycles
The Strychnos alkaloids have long been regarded as landmark targets for chemical synthesis due to their captivating architectures and notorious biological properties. family has fascinated synthetic medicinal chemists almost 100 years, since the decades-long debate over structure of 'flagship' member strychnine, its first total by Woodward. Featuring a dense array carbo- heterocyclic rings, numerous stereochemical challenges, these molecules inspired many strategies. In spite this rich...
Key words parallel kinetic resolution - β-amino alcohols aziridines chiral phosphoric acids