Chirality Transfer in Organic Synthesis (6 credits)
Prof. Giuseppe Faita
a. Introduction – Nomenclature
In the introduction will be discussed the basic concepts and the terminology of organic stereochemistry.
b. Chiral auxiliary approach
It will be discussed the use of mono- and bidentate chiral auxiliaries in diastereoselective synthesis. Particular attention will be given to the results obtained in the Diels-Alder reaction.
c. Asymmetric catalysis in organic synthesis.
The results obtained by using different kinds of asymmetric catalysts will be compared in several reactions taken as a reference benchmark.
d. Bis- and tris-oxazolines as chiral ligands
After the analysis of the different synthetic strategies in the literature, the structure of the chiral catalyst with several cations will be inferred, also by discussing their x-ray structura (when available). The use of BOX with different spacers and TOX as chiral ligands in several asymmetric catalyzed reactions will be presented. When possible, the catalytic cycle will be depth and, starting from the structure of the reacting intermediates, a rationale of the stereochemical outcome will be proposed.
e. Organocatalysis
The basic concepts and the principal synthetic applications of organic chiral messengers without any cation in asymmetric synthesis will be illustrated.