Elements of symmetry and chirality. Stereogenic elements. Descriptors for chirality. Prochirality and prostereogenicity. Chirality and optical activity. Racemic resolution. Kinetic resolutions and dynamic kinetic resolutions. Circular dichroism and RX methods for the determination of absolute configuration. Conformations of acyclic, cyclic, and heterocyclic systems. Dynamic NMR spectroscopy
Stereochemistry of Organic Compounds
Ernest L. Eliel, Samuel H. Wilen
ISBN: 978-0-471-01670-0
1267 pages
September 1994
Wiley
Learning Objectives
The objective of this course is to widen the knowledge of organic stereochemistry acquired by the student during the preceding cycle of study. The student will be able to recognize the chirality elements present in a molecule and assign the its configuration, to choose the best method for the determination of the enantiomeric composition of a chiral compound, the separation of enantiomers and the quantitative determination of the relative and absolute configuration.
Teaching Methods
frontal lessons
Type of Assessment
Oral examination
Course program
Symmetry elements and chirality: asymmetric and dissymmetric molecules. Symmetry operations. Stereogenic elements: stereogenic centers, axes and planes. Inherent chirality. Descriptors for central, axial and planar chirality. Molecules with stereogenic centers different from C (N, P, S, Si). Molecules with multiple stereogenic centers. Configuration descriptors. Homotopic, enantiotopic and diastereotopic groups and faces. Prochirality. Desymmetrization of achiral compounds. Optical activity and chirality. Racemic resolutions. Kinetic resolutions. Methods for the determination of the enantiomeric excesses (NMR, GLC, HPLC, optical rotation). Circular dichroism and application to the determination of the absolute configuration of the organic compounds and secondary structures of peptides. X-ray methods for determination of the absolute configuration of the organic compounds. Conformational analysis of acyclic and cyclic compounds. Dynamic NMR spectroscopy.