Lecture

Palladium-Catalyzed Asymmetric Reactions: Mechanisms and Applications

Graph Chat

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.

In course

CH-435: Asymmetric catalysis for fine chemicals synthesis

The asymmetric synthesis of fine chemicals is a research topic of growing importance for the synthesis of modern materials, drugs and agrochemicals. In this lecture, the concepts of asymmetric catalysis for fine chemical synthesis are introduced. ...

Description

This lecture discusses the palladium-catalyzed asymmetric decarboxylative addition of beta-keto acids to heteroatom-substituted allenes. It begins with an introduction to the reaction mechanism, highlighting the role of palladium and the ligand system in achieving high enantioselectivity. The instructor presents the first asymmetric branch-selective hydrofunctionalization of amidoallenes, detailing the nucleophile and electrophile involved in the reaction. The lecture emphasizes the significance of the reaction conditions, including temperature and time, in optimizing yields and selectivity. Critical analyses of the novelty, practicality, and sustainability of the reaction are provided, noting the mild conditions and the generation of carbon dioxide as a byproduct. The discussion also covers the potential for post-functionalization of alkoxyallenes and the implications for total synthesis. The lecture concludes with a Q&A session, encouraging students to engage with the material and explore the intricacies of the reaction mechanisms presented.

This video is available exclusively on Mediaspace for a restricted audience. Please log in to MediaSpace to access it if you have the necessary permissions.

Watch on Mediaspace

Instructor

Jérôme Waser

Jérôme Waser biography and CV's are available on the following website: http://lcso.epfl.ch/waser

Official source

Related concepts (32)

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

Catalysis

Catalysis (kəˈtæləsɪs) is the process of change in rate of a chemical reaction by adding a substance known as a catalyst (ˈkætəlɪst). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical reaction occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of an overall chemical reaction. The detailed steps of a reaction are not observable in most cases. The conjectured mechanism is chosen because it is thermodynamically feasible and has experimental support in isolated intermediates (see next section) or other quantitative and qualitative characteristics of the reaction.

Chemical reaction

A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive elements where both electronic and nuclear changes can occur.

Related lectures (42)

Retrosynthesis: Complex Fragments Synthesis Strategy

Explores the retrosynthesis strategy for complex fragments synthesis, using Leucascandrolide A as a case study.

Reaction Kinetics: Temperature Influence

Discusses temperature's impact on reaction rates, activation energy, collision efficiency, reaction mechanisms, catalysis, and enzymatic catalysis.

Chemical Reaction Mechanisms: Chain React

Explores reaction mechanisms, chain reactions, catalysis, enzyme catalysis, galvanic cells, and electromotive force in batteries.

Carbene Chemistry: Fundamentals and Applications

Explores the fundamentals and applications of carbene chemistry in organic synthesis and material science.

Hydrogenation Mechanism