Department of Organic Chemistry » Stereoselective synthesis (OCH/PGSS)

Stereoselective synthesis (OCH/PGSS)

Course Guarantor

Jan Hlaváč

Form of course completion:

Exam

Annotation:

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.

Content:

  • Terminology, Stereoselective synthesis, Categories of Stereoselective Synthesis, Convergent Syntheses, Diastereoselective Synthesis of Achiral
  • Strategies for Stereocontrol in Diastereoselective Synthesis
  • Diastereoselective Syntheses Based on Chiral Substrates of Natural Origin
  • Nucleophilic Additions, Electrophilic Reactions of Alkenes
  • The Aldol Reaction, Pericyclic Reactions
  • Catalytic Hydrogenations, Free Radical Reactions
  • Enantioselective Syntheses with Chiral Nonracemic Reagents
  • Enantioselective Syntheses with Chiral Nonracemic Catalysts
  • Nonlinear Effects in Catalysis, Enzyme Based Processes
  • Enantioselective Synthesis Involving Discrimination between Enantiotopic Groups, Enantioconvergent Syntheses
  • Interactions between Principal Chiral Reactants, Reagent Control, Kinetic Amplification

Literature:

  • Procter, G. Stereoselectivity in Organic Synthesis. Oxford University Press, Oxford, UK, 1998.
  • Original papers relevant to the topic
  • Eliel, E. L. Stereochemistry of Organic Compounds. John Wiley & Sons, New York, USA, 1994.
  • Atkinson, R. S. Stereoselective Synthesis. John Wiley & Sons, New York, USA, 1995.