Lecture

Catalytic Asymmetric Reactions in Organic Chemistry

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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 the principles and mechanisms of catalytic asymmetric reactions in organic chemistry, focusing on key topics such as Lewis and Brønsted acids activation of carbonyl and imines, Aldol Reaction, Allylation and Ene Reactions, and other nucleophiles for carbonyl addition. The instructor discusses important catalysts, applications, and the non-linear effect observed in some reactions. Various catalysts and their applications are explored, including the Keck allylation with Ti-Binol catalysts and the oxidation of products with ozone. The lecture also delves into the kinetic resolution of chiral compounds, desymmetrization, and the Mannich Reaction.

Instructor

Jérôme Waser

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

Official source

Ontological neighbourhood

Chemistry

Inorganic chemistry: Topics in inorganic chemistry

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.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.

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.

Mannich reaction

In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl () functional group by formaldehyde () and a primary or secondary amine () or ammonia (). The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

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Catalytic Asymmetric Reactions

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Organic Chemistry: Acid-Base Reactions and Electronegativity

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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 in Organic Chemistry

Covers catalytic asymmetric reactions, including activation of electrophiles, use of iodine reagents, and various catalytic reactions in organic chemistry.

Chemistry of Imines and Enamines

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

Related concepts (32)

Lewis acids and bases

Acid

Aldol reaction

Brønsted–Lowry acid–base theory

Mannich reaction