A5025924300- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Axial and Atropisomeric Chirality Synthesis
- Asymmetric Hydrogenation and Catalysis
- Chemical Synthesis and Analysis
- Chemical Synthesis and Reactions
- Oxidative Organic Chemistry Reactions
- Carbohydrate Chemistry and Synthesis
- Molecular spectroscopy and chirality
- Synthetic Organic Chemistry Methods
- Microbial Natural Products and Biosynthesis
- Radical Photochemical Reactions
- Enzyme Catalysis and Immobilization
- Vanadium and Halogenation Chemistry
- Fluorine in Organic Chemistry
- Chemical synthesis and alkaloids
- Plant biochemistry and biosynthesis
- Sulfur-Based Synthesis Techniques
- Cyclopropane Reaction Mechanisms
- Organoboron and organosilicon chemistry
- Synthesis of Indole Derivatives
- Synthesis and Catalytic Reactions
- Crystallography and molecular interactions
- Chemical Reactions and Isotopes
- Origins and Evolution of Life
Max-Planck-Institut für Kohlenforschung
2018-2024
RWTH Aachen University
2016-2018
University of California, Berkeley
2017
Abstract The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)‐catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access 1,4‐diamino‐2‐butynes, which contrasts classical approaches that provide propargylamine‐type products. Solventless milling conditions were found be essential unmask 3 products with new compositions.
Abstract Mechanochemical activation of iron cyano complexes by ball milling results in the formation HCN, which can be trapped and incorporated into α‐aminonitriles. This prebiotic impact scenario extended mechanochemically transforming resulting α‐aminonitriles α‐amino amides using a chemical route related to early Earth conditions.
A mechanochemical version of the Strecker reaction for synthesis α-aminonitriles was developed. The milling aldehydes, amines, and potassium cyanide in presence SiO2 gave corresponding good to high yields. efficiency Strecker-type multicomponent allowed one-pot tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
Despite tremendous advances in enantioselective catalysis of the Diels–Alder reaction, use simple α,β-unsaturated esters, one most abundant and useful class dienophiles, is still severely limited scope due to their low reactivity. We report here a catalytic asymmetric methodology for large variety methyl esters different dienes based on extremely reactive silylium imidodiphosphorimidate (IDPi) Lewis acids. Mechanistic insights from accurate domain-based local pair natural orbital...
Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes direct oxidation of sulfides a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition form chiral cyclic N,S-acetals with moderate high enantioselectivites. Deuterium-labelling experiments were performed identify stereodiscrimination step this process. Further analysis...
Abstract Mechanochemical activation of iron cyano complexes by ball milling results in the formation HCN, which can be trapped and incorporated into α‐aminonitriles. This prebiotic impact scenario extended mechanochemically transforming resulting α‐aminonitriles α‐amino amides using a chemical route related to early Earth conditions.
Abstract Polyene cyclizations are among the most complex and challenging transformations in biology. In a single reaction step, multiple carbon–carbon bonds, ring systems stereogenic centres constituted from simple, acyclic precursors 1–3 . Simultaneously achieving this kind of precise control over product distribution stereochemistry poses formidable task for chemists. particular, polyene cyclization (3 E ,7 )-homofarnesol to valuable naturally occurring ambergris odorant (−)-ambrox is...
Abstract The ability of mechanochemistry to alter established chemical selectivity is demonstrated. A copper(I)‐catalyzed mechanochemical aldehyde/alkyne/amine coupling using calcium carbide as the acetylene source provides selective access 1,4‐diamino‐2‐butynes, which contrasts classical approaches that provide propargylamine‐type products. Solventless milling conditions were found be essential unmask 3 products with new compositions.
A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, KCN afforded library α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by lignocellulosic biomass as additives. Particularly, commercially available Kraft lignin found to be the best activator for addition cyanide in situ formed imines. comparative study 31P-NMR (Nuclear Magnetic Resonance) along with IR (Infrared) data...
Abstract An enantioselective synthesis of cyclopentenediones bearing a pyrazole unit has been achieved through an organocatalytic Michael addition/oxidation process. This desymmetrization reaction led to the desired pyrazole‐cyclopentenediones with high yield and good enantioselectivities. The postulated cross‐dehydrogenative coupling‐mechanism investigated via preliminary control experiments. magnified image
Key words Knoevenagel condensation - iminium ion catalysis aminocatalysis α,β-unsaturated esters
Abstract Reported is the first enantioselective oxidative Pummerer‐type transformation using phase‐transfer catalysis to deliver enantioenriched sulfur‐bearing heterocycles. This reaction includes direct oxidation of sulfides a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition form chiral cyclic N , S ‐acetals with moderate high enantioselectivites. Deuterium‐labelling experiments were performed identify stereodiscrimination step this process. Further...
Key words amine oxidase - ene-imine reductase chemo-enzymatic dearomatization piperidine synthesis
Key words asymmetric amine catalysis - steroid synthesis proline Robinson annulation
Key words pericyclase - intramolecular Diels–Alder reaction cis-decalin shape complementarity
Key words amidophosphates - halocyclization chromans Lewis acid organocatalysis pyrrolidines
Key words atroposelectivity - allylic alkylation anilides biscinchona alkaloids Lewis base catalysis Morita–Baylis–Hillman carbonates
Key words dihydrobenzofurans - stereodynamics redox chemistry kinetic resolution
Key words enantioconvergence - redoxisomerization pyranones dehydrogenases
Key words Prins reaction - semipinacol rearrangement cascade pinenes fenchones Brønsted acid catalysis
Key words sorbicillinoids - chemo-enzymatic total synthesis oxidative dearomatization
Key words C–H alkylation - directed evolution heme protein iron catalysis
Key words anion-binding catalysis - pyrylium salts dearomatization enantioselectivity