Lecture

Catalytic Asymmetric Reactions in Organic Chemistry

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.

Description

This lecture covers the principles of catalytic asymmetric reactions in organic chemistry, focusing on Lewis and Brønsted acids activation of carbonyl and imines. Topics include LUMO activation, Lewis acid catalysis, and various types of reactions such as Aldol, Mannich, and Diels Alder. The instructor discusses the use of chiral catalysts, ligands, and the role of different nucleophiles in achieving high enantioselectivity.

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

Official source

Related concepts (32)

Lewis acids and bases

A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons.

Acid

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents.

Brønsted–Lowry acid–base theory

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

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.

Acid–base reaction

An acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory. Their importance becomes apparent in analyzing acid–base reactions for gaseous or liquid species, or when acid or base character may be somewhat less apparent.

Related lectures (64)

Chemistry of Imines and Enamines

Explores the chemistry of imines and enamines, including amine condensation, ketone-iminium reduction, and the use of chiral auxiliaries.

Catalytic Asymmetric Reactions in Organic Chemistry

Explores catalytic asymmetric reactions in organic chemistry, covering Lewis and Brønsted acids activation, Aldol Reaction, Allylation, Ene Reactions, and more.

Catalytic Asymmetric Reactions in Organic Chemistry

Explores catalytic asymmetric reactions in organic chemistry, focusing on proline-catalyzed reactions and amination of aldehydes and ketones.

Catalytic Asymmetric Reactions

Covers various catalytic asymmetric reactions in organic chemistry, including Lewis and Brønsted acids activation, Jacobsen Urea Catalyst, and Mannick Reaction.

Asymmetric Synthesis: Carbonyl Additions and Chelation

Explores asymmetric synthesis through carbonyl additions and chelation, emphasizing selectivity and key concepts like Felkin-Anh model.

Related concepts (32)

Lewis acids and bases

Acid

Brønsted–Lowry acid–base theory

Enantioselective synthesis

Acid–base reaction