Lecture

Bifunctionalized Compounds: Strategies and Selectivity

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In course

CH-335: Asymmetric synthesis and retrosynthesis

The first part of the course presents the classical methods of asymmetric synthesis. The second part of the course introduces retrosynthesis strategies based on the disconnection approach. ...

Description

This lecture covers the synthesis strategies and regioselectivity of bifunctionalized compounds, focusing on the selective enolization and electrophilic reactions of carbonyls. It also discusses the control of partners in the Eldolization process, the choice of disconnections, and the chiral auxiliaries used for selective enolization. The instructor explains the principles behind the strategies for bifunctionalized compounds, such as the Beyer-Villiger oxidation and coordination laws, emphasizing the importance of regioselectivity and stereoselectivity in organic synthesis.

Instructors (2)

Sandrine Gerber

Sandrine Gerber studied chemistry at the "Ecole Nationale Supérieure de Chimie de Paris" in France, where she obtained a diploma of chemical engineer in 1993. The same year she obtained a DEA (Master degree) of organic chemistry at the University Pierre et Marie Curie (Paris VI, France). From 1993 to 1996 she did a PhD in organic chemistry under the supervision of Prof. Jean-Pierre Genêt at the Ecole Nationale Supérieure de Chimie de Paris. In 1996, she moved to University of Lausanne for a post-doctoral stay under the supervision of Prof. Pierre Vogel. In 1998, she was appointed Maître-Assistante at the Institute of Organic Chemistry in the University of Lausanne. In 2003, she obtained the habilitation to direct research from the University Pierre et Marie Curie (Paris VI, France). The same year, she was appointed scientific adjunct at the EPFL and senior scientist (Maître d'Enseignement et de Recherche) in 2006. In December 2014, she was promoted to titular professor. Since September 2007, Sandrine Gerber is deputy to the director of the Institute of Chemical Sciences and Engineering (ISIC). She is also member of the Board of Directors of the Swiss Chemical Society. Since 2007, Sandrine Gerber is part-time lecturer at the university of Fribourg. She was awarded the Prize Eugene Schueller in 1997, the Prize Dufour for prospective organic chemistry in 2005 and the Werner Prize 2010. She also received a special mention in recognition of exceptional quality of pedagogic competencies in the teaching of basic sciences, given by the Direction of the School of Biology and Medicine from the University of Lausanne, in 2013. In October 2018, she will receive the Prize for Excellence in Teaching from the section of Chemistry and Chemical Engineering.

Stefano Nicolai

Teaching & PhD Courses Asymmetric synthesis and retrosynthesis CH-335 The first part of the course presents the classical methods of asymmetric synthesis. The second part of the course introduces retrosynthesis strategies based on the disconnection approach.

Official source

Related concepts (32)

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.

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.

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: total synthesis, semisynthesis, and methodology.

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.

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior.

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