After successful completion of the course, students are able to carry out a retrosynthonal disconnection of a molecule of medium complexity and write down a reasonable forward synthesis considering knowledge from Organic Chemistry courses. They know the basics of stereochemistry and stereoselective synthesis, and the application of molecular orbital theory to describe organic chemical reactions.
Module 1: Strategies in Synthesis Planning: Principals of retrosynthesis, strategies for the design of monofunctional aliphatic and cycloaliphatic structures as well as aromatic substitution pattern; concepts for the synthesis of di- and polyfunctional products in dependence from the distance of the functional groups; umpolung of reactivity; latent functionalities. Strategies for building up heterocyclic ring systems. General concepts for the synthesis of more complex organic structures. Protecting groups chemistry (Prerequisites for protecting groups; concept of orthogonal protecting groups; Introduction, cleavage and selectivity of protecting groups for importantfunctional groups like alcohols, diols, amines, carbonyl groups, and carboxylic acids).
Module 2: Foundations of stereochemistry and stereoselective syntheses: Structure, stereoisomerism, symmetry, configuration, properties of stereoisomers, chiro-optical properties, separation of stereoisomers, heterotope ligands and planar structures, stereochemistry of alkenes, conformation of acyclic molecules, configuration and conformation of cyclic molecules, chirality of molecules without chiral centres. Asymmetric synthesis: chiral auxilaries; chiral reagents; several types of reactions; non-linear effects; Zimmermann-Traxler-model; double stereodifferentiation.
Module 3: Molecular orbitals and organic chemical reactions: Molecular orbital theory and its implications for the structure and reactivity (incl. kinetics) of organic molecules.
Module 1: Retrosynthesis is demonstrated on board by M. Schnürch with constant questions to the students.
Module 2: Advanced stereochemistry and concepts of asymmetric synthesis will be described and discussed.
Module 3: The implications and applications of molecular orbital theory will be described in a simplified non-mathematical form and discussed with the students by means of and supported by several examples.
1. Block-VO Schröder (module 2)
2. Block-VO Schnürch (module 1)
3. Block-VO Mikula (module 3)
Written exam (120 min) on the content of all three parts of this course:
- Retrosynthesis: 2 question (2 x 20 points)
- Stereochemistry/Asymmetric synthesis: 4 questions (4 x 10 points)
- Molecular orbital theory: 2 questions (2 x 10 points)
A maximum of 100 points can be reached. Grades: S1 (89-100), U2 (76-88), B3 (63-75), G4 (50-62) and N5 (<50). In the case of N5 the exam needs to be repeated to complete this course.
