73056 - Methods for the Study of Chirality

Learning outcomes

The main goal of the course is to provide the student with both theoretical and practical backgrounds on: symmetry, molecular chirality and related concepts; main instrumental techniques for stereochemical characterization of organic molecules, biopolymers and supramolecular systems (circular dichroism, NMR, chromatographic methods, nematic liquid crystals, polarimetry, X ray diffraction); methods for the preparation of enantiopure compounds and techniques for the determination of optical purity and absolute configuration. At the end of the course the student achieves a deep understanding of organic stereochemistry and can autonomously perform research in the field.

Course contents

1) The molecular symmetry

2) Chirality and stereogenicity. Topicity relationships 

3) Stereogenic units. Prochirality e prostereogenicity

4) Configuration descriptors

5) Physical manifestation of chirality. The role of chirality in biological systems

6) Stereoisomeric enrichment: resolutions and stereoselective transformations

7) Determination of the enantiomeric excess (Polarimetry, NMR, cromatographic methods)

8) Determination of relative and absolute configuration (Chemical correlation, X-ray diffraction, HPLC, NMR, Circular dichroism, Liquid crystal methods)

9) Special topics derived from recent literature

Readings/Bibliography

E.L. Eliel, S.H. Wilen, "Stereochemistry of Organic Compounds" Wiley Interscience, 1994

Teaching methods

Lectures

Assessment methods

The final examination, aiming atascertaining the student's acquired skills, consists of an oral presentation pertaining a specific topic related to the course main contents. The subject will be agreed between the student and the teacher, who will provide the relevant literature. The presentation will be followed by a brief discussion.

Teaching tools

Presentations. Files of presentations will be available for download.

Office hours

See the website of Stefano Masiero