Educational guide 2013_14 Faculty of Chemistry

Synthesis, Catalysis and Molecular Design (2013)

Contents

Topic	Sub-topic
1. Stereochemistry of organic compounds. Prochirality and prostereoisomerism. Homotopy and heterotopy. Nomenclature of stereoheterotopic groups and faces The concept of conformation. Conformational analysis Working methods in conformational analysis. Absolute configuration and relative configuration. Determining absolute configuration.
2. Introduction to asymmetric synthesis - Strategies in the synthesis of enantiomerically enriched compounds. Racemate resolution and asymmetric synthesis. Methods for determining enantiomeric excess. Specific optic rotation, gas and liquid chromotography, nuclear magnetic ressonance.
3. Use of chiral auxiliaries - Chiral Auxiliaries. Introduction. -Asymmetric additions to carbonyls. Analysis of possibilities. Alkylation of enolates - a representative example. Chiral auxiliaries in acids and derivatives. Chiral auxiliaries in aldehydes and ketones. Effective methods using chiral auxiliaries.
4. Asymmetric reagents - Enantioselective protonations and deprotonations. Reducing agents of boron and aluminium. Allylation reactions with B and Ti reagents. Chiral organometallics reagents of Zn and Cu. Expoxidation with chiral dioxiranes
5. Asymmetric catalysis with metals: hydrogenation (alkenes, ketones, imines), oxidation, other reactions (allylic alkylation, allylation, hydroboration, Heck, etc.). Reactions catalysed by Lewis acids. Ketone reduction catalysed by oxazaborolidines.
6. Organocatalysis. Reactions catalysed by acids and bases.
7. Enzymatic catalysis. Dynamic enzymatic resolution.
8. Industrial methods. Examples of the use of different asymmetric synthesis strategies Integrated discussion and compared analysis.

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Assessment	Sources of information	Recommendations