OVERVIEW

Complements of Organic Chemistry is one of the main courses of the Master's Degree in Chemical Sciences, specifically activated for the curriculum Organic Chemistry applied to Material and Life Science. The topics covered are chosen in such a way as to revisit in particular reactions seen in the basic courses but with an in-depth study aimed most of all at understanding the stereochemical aspects. Particular emphasis is placed on the use of the most modern methodologies, in particular of the catalytic type, capable of positively influencing the stereochemical outcome of stereoselective reactions.

AIMS AND CONTENT

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.

TEACHERS AND EXAM BOARD

Exam Board

RENATA RIVA (President)

LISA MONI

ALESSANDRO PELLIS

LUCA BANFI (President Substitute)

CHIARA LAMBRUSCHINI (Substitute)

LESSONS

LESSONS START

From February, 26, 2024

EXAMS

EXAM DESCRIPTION

The exam consists of an oral test, divided into two parts:

1. an interview in which the student is asked 2-3 general questions on the topics covered in class;
2. a presentation in which the student, thanks to the projection of a series of slides prepared by himself, critically exposes the results contained in 1-2 very recent scientific papers on topics consistent with the program, which have been assigned to him by the teacher at least one week before the exam. The presentation is interactive, and the teacher will verify the understanding of the topics presented by asking the student questions.

ASSESSMENT METHODS

The exam, exclusively in oral form, is conducted by two tenured teachers and lasts at least 30 minutes.

In this way, the commission is able to verify with high accuracy the achievement of the learning outcomes of the course. In particular, during the interview the degree of understanding of the topics developed in class is ascertained while, during the presentation, the ability to understand a scientific article is ascertained, thanks also to the help of the topics learned during the lessons.

When the learning outcomes are not achieved, the student is invited to deepen the study and to take advantage of further explanations by the teacher.

Exam schedule