LEARNING OUTCOMES

The aim of the course is to study the concepts of organic stereochemistry and their applications to the most advanced problems of stereoselective organic synthesis. The acquisition of knowledge is envisaged in the following topics: a) methodologies that allow asymmetric induction; b) analytical techniques for evaluating the stereoselectivity of reactions; c) interpretative models of the experimental stereochemical results. Added to this are the ability: a) to critically interpret specific literature; b) to apply to practical cases some of the most efficient and modern strategies for producing enantiomerically enriched molecules, with particular attention to the construction of C-C and C=C bonds, also with the use of organometallic catalysis and organocatalysis.

AIMS AND LEARNING OUTCOMES

The aim of the course is to study the concepts of organic stereochemistry and their applications to the most advanced problems of stereoselective organic synthesis. The acquisition of knowledge is envisaged in the following topics: a) methodologies that allow asymmetric induction; b) analytical techniques for evaluating the stereoselectivity of reactions; c) interpretative models of the experimental stereochemical results. Added to this are the ability: a) to critically interpret specific literature; b) to apply to practical cases some of the most efficient and modern strategies for producing enantiomerically enriched molecules, with particular attention to the construction of C-C and C=C bonds, also with the use of organometallic catalysis and organocatalysis.

Specifically, the student will be able to:

• correctly establish complex synthetic pathways that require the control of stereochemistry in the consecutive formation of stereocenters (internal and relative asymmetric induction and double stereodifferentiation);
• analyze the stereochemical results of stereoselective reactions in order to optimize the reaction under study;
• correctly use the most modern methods for the effective determination of the enantiomeric excess and/or the diastereomeric ratio.

PREREQUISITES

A good knowledge of basic organic chemistry.

TEACHING METHODS

The course is divided into lectures on the topics covered by the program. The files with the presentations of the lessons are available on Aulaweb.

SYLLABUS/CONTENT

• Advanced stereochemistry concepts: a) symmetry properties of organic molecules: symmetry elements and point groups; b) conformations of acyclic and cyclic molecules; c) chirality of molecules without stereogenic centers (allenes, biphenyls, etc.); d) prostereoisomerism
• Methods for the experimental determination of the enantiomeric excess
• Enantio- and diastereoselective reactions [stoichiometric reactions, catalytic reactions (organometal catalysis and organocatalysis), use of chiral auxiliaries]
• Examples of enantio- and diastereoselective reactions: reductions of C=C and C=O bonds, C-C and C=C bond forming reactions, oxidations etc. In particular catalytic reaction will be deeper investigated
• Claisen rearrangement
• [4+2] Cycloadditions: the Diels-Alder reaction

RECOMMENDED READING/BIBLIOGRAPHY

Being a rather specialized course there are no textbooks. The didactic material made available on Aulaweb and the notes taken in class are essential for the preparation of the exam. Interested students can however ask the teacher for bibliographic material for further information.