Embedded Files
Synthesis • Methods • Catalysis
Synthesis • Methods • Catalysis
Overview
Overview
Our research focuses on the development of new synthetic methodologies based on the application of pericyclic reactions, transition metals, organocatalysis, Ni-, Co-, Cu-, and Pd-catalysed organic transformations, and photochemically and electrochemically driven organic reactions. We mainly concentrate on creating new methods to make specific types of organic compounds that are important for biology and medicine, such as amino acids, peptidomimetics, alkaloids, carbohydrates,
Our research focuses on the development of new synthetic methodologies based on the application of pericyclic reactions, transition metals, organocatalysis, Ni-, Co-, Cu-, and Pd-catalysed organic transformations, and photochemically and electrochemically driven organic reactions. We mainly concentrate on creating new methods to make specific types of organic compounds that are important for biology and medicine, such as amino acids, peptidomimetics, alkaloids, carbohydrates,
Hydro- & difunctionalisation of allylic alcohols and amines
Hydro- & difunctionalisation of allylic alcohols and amines
Novel protocols for the preparation of allylic alcohols and amines
Novel protocols for the preparation of allylic alcohols and amines
Organic electrochemistry
Organic electrochemistry
Electrochemistry offers a mild, efficient, and sustainable alternative to conventional chemical approaches for organic redox transformations. With the help of an electrode and a power source, chemists are bestowed with an imaginary reagent whose potential can be precisely dialled in.
Our group works on using organic electrosynthesis to create highly reactive substances that are difficult or dangerous to make with regular methods. Our research aims to improve new methods that use electrochemistry to start and help complex organic reactions, making it safer and easier to handle reactive substances. By using electricity, which is a clean and usually easy-to-get resource, our methods greatly reduce the need for harmful chemical substances and cut down on waste, showing a more eco-friendly way to make chemicals. This special approach makes it easier and better for the environment to carry out complex chemical processes, while also opening up new possibilities for research and industry, such as the development of sustainable materials and pharmaceuticals, making our methods a greener and safer choice in organic chemistry.
Extreme Potentials via e-PRC or conPET strategies
Extreme Potentials via e-PRC or conPET strategies
Our group aims to utilise electronically unstable intermediates to facilitate complex reactions while preserving selective control. Photoredox catalysis has proven to be very effective in handling different functional groups and achieving great selectivity in radical reactions. However, substrate classes that require high activation potentials are excluded from photoredox catalysis due to the insufficient energy supplied by visible light. Our study focuses on using a novel class of photocatalysts, organic photocatalyst radical ions, that exhibit low reactivity in their ground state but transform into powerful redox agents upon excitation. This is executed either by electrochemically mediated photoredox catalysis (e-PRC) or consecutive photo-induced electron transfer (conPET). These techniques activate previously inert substrate classes for radical chemistry while maintaining the selectivity profile typical of traditional photoredox catalysis.
Allyl cyanate-to-isocyanate [3,3]-sigmatropic rearrangement
Allyl cyanate-to-isocyanate [3,3]-sigmatropic rearrangement
The cyanate-to-isocyanate rearrangement (specifically the allyl cyanate/isocyanate rearrangement) is an effective process that changes allylic alcohols into protected allylic
It is a concerted [3,3]-sigmatropic rearrangement (similar to a hetero-Cope rearrangement) typically proceeding via a chair-like transition state, resulting in a complete [1,3] chirality transfer. This means the stereochemical information of the starting material is perfectly preserved in the product. This rearrangement happens on its own at or below room temperature, unlike many other sigmatropic shifts that need metal catalysts. The rearrangement is effectively irreversible because the resulting isocyanate is significantly more stable than the starting cyanate.
In practice, allyl cyanates are often too unstable to isolate and are generated in situ from the corresponding allyl carbamates. The latter ones are stable, mostly crystalline, easy-to-handle compounds readily available from allylic alcohols. A common practical realisation of this rearrangement includes a 3-step sequence realised in a one-pot manner. Firstly, allyl carbamate is dehydrated to form an intermediate allyl cyanate. The unstable cyanate immediately undergoes the [3,3]-shift to form an allyl isocyanate. Finally, the highly reactive isocyanate is "trapped" by a nucleophile (like an alcohol, amine, C-nucleophile, thiol or even hydride reagent) to yield stable allylamine derivatives, like carbamates, amides, ureas, etc.
Synthesis of non-racemic multisubstituted allylic alcohols
Synthesis of non-racemic multisubstituted allylic alcohols
Synthesis of non-racemic multisubstituted allylic alcohols
Synthesis of non-racemic multisubstituted allylic alcohols
Google Sites
Report abuse