|
Lecturer(s)
|
-
Hlaváč Jan, prof. RNDr. Ph.D.
|
|
Course content
|
1) Terminology, Stereoselective synthesis, Categories of Stereoselective Synthesis, Convergent Syntheses, Diastereoselective Synthesis of Achiral 2) Strategies for Stereocontrol in Diastereoselective Synthesis 3) Diastereoselective Syntheses Based on Chiral Substrates of Natural Origin 4) Nucleophilic Additions, Electrophilic Reactions of Alkenes 5) The Aldol Reaction, Pericyclic Reactions 6) Catalytic Hydrogenations, Free Radical Reactions 7) Enantioselective Syntheses with Chiral Nonracemic Reagents 8) Enantioselective Syntheses with Chiral Nonracemic Catalysts 9) Nonlinear Effects in Catalysis, Enzyme Based Processes 10) Enantioselective Synthesis Involving Discrimination between Enantiotopic Groups, Enantioconvergent Syntheses 11) Interactions between Principal Chiral Reactants, Reagent Control, Kinetic Amplification
|
|
Learning activities and teaching methods
|
|
Lecture
|
|
Learning outcomes
|
Spatial arrangement of atoms in a molecule is fundamental for physical-chemical properties and biological activity. A simple difference of the spatial arrangement in a molecule may bring completely different properties. Knowledge of stereochemical rules and course of stereoselective reactions enables synthesis of desired stereoizomers. The course is focused on basic principles of stereoselective synthesis. 1) Terminology, Stereoselective synthesis, Categories of Stereoselective Synthesis, Convergent Syntheses, Diastereoselective Synthesis of Achiral 2) Strategies for Stereocontrol in Diastereoselective Synthesis 3) Diastereoselective Syntheses Based on Chiral Substrates of Natural Origin 4) Nucleophilic Additions, Electrophilic Reactions of Alkenes 5) The Aldol Reaction, Pericyclic Reactions 6) Catalytic Hydrogenations, Free Radical Reactions 7) Enantioselective Syntheses with Chiral Nonracemic Reagents 8) Enantioselective Syntheses with Chiral Nonracemic Catalysts 9) Nonlinear Effects in Catalysis, Enzyme Based Processes 10) Enantioselective Synthesis Involving Discrimination between Enantiotopic Groups, Enantioconvergent Syntheses 11) Interactions between Principal Chiral Reactants, Reagent Control, Kinetic Amplification
Evaluate the effectiveness of stereoselective synthetic methods, choose the suitable method for a given purpose.
|
|
Prerequisites
|
unspecified
|
|
Assessment methods and criteria
|
Oral exam
The exam is performed orally. Students must demonstrate sufficient understanding of all the topics listed in the course content. - Basic characterization of optically active compounds - stereoisomerism and prostereoisomerism - asymmetric induction, and chiral catalysis - Methods for determination of optical purity - NMR analysis of the optical isomers
|
|
Recommended literature
|
-
Původní vědecké práce.
-
Atkinson, R.S. (1995). Stereoselective Synthesis. John Wiley & Sons, New York, USA.
-
Eliel, E.L. (1994). Stereochemistry of Organic Compounds. John Wiley & Sons, New York, USA.
-
Procter, G. (1998). Stereoselectivity in Organic Synthesis. Oxford University Press, Oxford, UK.
|