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Lecture

Catalytic Asymmetric Reactions in Organic Chemistry

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 summary of chapters 3.1 and 3.2, focusing on catalytic asymmetric reactions in organic chemistry. It discusses the activation of electrophiles other than carbonyl/imines, the use of hypervalent iodine reagents, and various catalytic reactions such as oxidative spirolactonization and diacetoxylation of olefins. The lecture also delves into the catalytic asymmetric Staudinger Aza-Wittig reaction, activation of allylic systems, direct allylic substitution, and sources of enantiodiscrimination. Furthermore, it explores ligands and mechanisms, stereoinduction models, desymmetrization of meso-substrates, and kinetic resolution of propargylic alcohols. The lecture concludes with discussions on chiral acylation, dynamic kinetic resolution of esters, and the resolution of cyclic amines via azolium intermediates.

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)

Kinetic resolution

In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials.

Chiral auxiliary

In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use. Most biological molecules and pharmaceutical targets exist as one of two possible enantiomers; consequently, chemical syntheses of natural products and pharmaceutical agents are frequently designed to obtain the target in enantiomerically pure form.

Michael addition reaction

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

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.

Asymmetric induction

Asymmetric induction (also enantioinduction) describes the preferential formation in a chemical reaction of one enantiomer or diastereoisomer over the other as a result of the influence of a chiral feature present in the substrate, reagent, catalyst or environment. Asymmetric induction is a key element in asymmetric synthesis. Asymmetric induction was introduced by Hermann Emil Fischer based on his work on carbohydrates. Several types of induction exist.

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Related concepts (32)

Kinetic resolution

Chiral auxiliary

Michael addition reaction

Enantioselective synthesis

Asymmetric induction