Lecture

Catalytic Asymmetric Reactions

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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 covers various catalytic asymmetric reactions in organic chemistry, including the use of Lewis and Brønsted acids for carbonyl and imine activation, the Jacobsen Urea Catalyst, and the Mannick Reaction. It also discusses the activation with phosphoric acids, Passerini and Ugi reactions, and the reduction of imines with Hantsch ester. The presentation delves into the Jacobsen and Maruoka methods, the Mannick Reaction, and the use of phosphoric acids for activation. Furthermore, it explores the activation of carbonyles for ene reactions, the use of carbenes and oxidation for activation, and the Aza Friedel-Craft reaction with electron-rich aromatic compounds.

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)

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.

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.

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.

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.

Acid strength

Acid strength is the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a proton, H+, and an anion, A-. The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions. HA -> H+ + A- Examples of strong acids are hydrochloric acid (HCl), perchloric acid (HClO4), nitric acid (HNO3) and sulfuric acid (H2SO4). A weak acid is only partially dissociated, with both the undissociated acid and its dissociation products being present, in solution, in equilibrium with each other.

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Catalytic Asymmetric Reactions in Organic Chemistry

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Catalytic Asymmetric Reactions in Organic Chemistry

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Lewis and Brønsted acids activation

Explores Lewis and Brønsted acids activation of carbonyls and imines, focusing on conjugate additions and cycloadditions, with examples of pioneering and recent/classical reactions.

Catalytic Asymmetric Reactions in Organic Chemistry

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Related concepts (32)

Acid

Lewis acids and bases

Brønsted–Lowry acid–base theory

Acid–base reaction

Acid strength