ADVANCED ORGANIC CHEMISTRY
Learning outcomes of the course unit
The course aims at providing to the students the knowledge of organic stereochemistry which allows them to understand the reactions of chirality transfer. New reactions will be presented to increase the student preparation in organic chemistry. Different kinds of reactions will be presented, also with stereoselectivity.
Particular attention will be always devoted to the discussion of results from the literature and examples of industrial application.
The main parameters involved in the study of reaction mechanism will be presented.
Course contents summary
Organic stereochemistry: molecular chirality due to center, axis, plane of chirality and elicity. Atropoisomerism. Chirooptical methods: polarimetry and circular dicroism (CD)and its application in configurational and conformational studies.
Study of dynamic phenomena by NMR spectroscopy. Determination of enantiomeric composition by chromatographic and NMR methods. Conglomerates. Racemate resolution: principles and discussion of industrial cases. Stereoselective and stereospecific reactions. 1,2-Rearrangements involving C, O and N atoms. Diastereo- and enantioselective syntheses. Aldolic condensations and epoxidation reactions. Enantioselective epoxidation promoted by Sharpless as well as Jacobsen-Katsuki chiral catalysts. Chirality amplification. Organoboranes in synthesis. Click-chemistry. Protective groups. C-C bond formation by cross-coupling reactions. Additional organic reactions (e.g. click chemistry). Structure-reactivity relationships. Solvent effect. Intramolecular catalysis.
F. A. Carey, R. A. Sundberg “Advanced Organic Chemistry” 5a Edizione Springer.
E.L. Eliel, S.H. Wilen “Stereochemistry of Organic Compounds” J.Wiley & Sons
E.V. Anslyn,D.A. Dougherty "Modern Physical Organic Chemistry" University Science Book, California
Bibliographic references on various topics will be given.
Transparencies and Power point slides will be employed and a copy will be given in advance to the students. References of original papers are furnished to permit a deeper study.
Assessment methods and criteria