MODERN STRATEGIES IN ORGANIC SYNTHESIS
Learning outcomes of the course unit
The main objective of the course is to give to the students the tools for an efficient design for the synthesis of complex organic compounds on the light of the request of the modern eco-compatible chemistry
It is requested the have attended the Organic Chemistry I and Organic Chemistry II courses and the related Laboratory courses
Course contents summary
Organic synthesis in the past and the modern criteria for making green synthetic processes. Retrosynthetic analysis. Order of events. One-group C-C disconnection. Disconnections 1,1-, 1,2- and 1,3-di C-X under direct and reversed polarity. One-C-C bond disconnection. Disconnection 1,1-, 1,2- and 1,3-di C-C. Sterocontrol. Stereospecific and stereoselctive processes. Carbonyl condensation. Disconnections 1,2-, 1,3-, 1,4-, 1,5- and 1,6-di C-O. Reconnection. Approach to cyclic and not aromatic heterocyclic systems. Access to 3, 4, 5, 6 and 7 ring systems. Kinetic and thermodynamic problems involved and choice of the best synthetic route. Pericyclic reactions. Kinetic and thermodynamic control in pericyclic reactions. Orbital symmetry role in thermal and photochemical processes. Electrocyclic reactions. Sigmatropic reactions. 2+2 and 4+2 cycloaddition reactions. 1,3-dipolar cycloadditions. Application of the empirical Woodward-Hoffmann rules.
1) F.A. Carey, R.J. Sundberg Advanced Organic Chemistry (3rd edition): Part B: Reactions and Synthesis; Plenum Press; 1990.
2) S. Warren Organic Synthesis, The Disconnection Approach Wiley and sons; 1982.
The course is organized in two parts: a theoretical part concerning the synthetic strategies and a second part with exercises concerning the synthesis of complex organic compounds.