Vorlesung "Fundamentals of Organic Stereochemistry"

1. History: Jean-Baptist Biot and Louis Pasteur

2. Static stereochemistry

2.1. Hybridization

2.2. C-C-bond lengths

2.3. Pauling-Brockway equation

2.4. C-C-C-bond angles

2.5. C-C-C-C-dihedral angles

2.6. Quantifications: ¹³C-¹H coupling constants

2.7. Isomerism

2.8. Enantiomerism

2.9. Representations: wedge-dash, saw horse, Newman, Fischer

2.10. The E/Z-specification

2.11. The R/S system of nomenclature

2.12. Nomenclature of relative and absoute configuration

2.12.1. d/l

2.12.2. D/L

2.12.3. erythro/threo

2.12.4 syn/anti

2.12.5. α/β-nomenclature of steroids

2.12.6. The r/c/t-system

2.13. Symmetry elements and point groups

2.14. Elements of chirality

2.14.1. Centers of chirality

2.14.2. Axes of chirality

2.14.3. Planes of chirality

2.15. Meso-Compounds and pseudoasymmetry

3. Optical activity

3.1. Lineraly polarized light

3.2. Circularly polarized light

3.3. ORD spectroscopy

3.3.1. The Fresnel equation

3.3.2. The Cotton effect

3.4. Circular dichroism

3.4.1. The octant rule

4. Isolation of enantiomers

5. Determination of optical purity

5.1. Chromatography

5.2. NMR-methods, lanthanide shift reagents

6. Dynamic stereochemistry

6.1. Mechanism controlled reactions

6.2. Asymmetric syntheses

6.2.1. Prochirality and topocity

6.2.2. Diastereoselective syntheses

6.2.2.1. Cram´s rule

6.2.2.2. Felkin´s rule

6.2.2.3. Chiral auxiliaries plus examples