SUPRAMOLECULAR AND ASYMMETRIC SYNTHESIS OF ORGANIC MOLECULES AND LABORATORY

The course aims to deepen the student's fundamental knowledge of organic chemistry. Common strategies for asymmetric synthesis and their reaction mechanisms will be analyzed in detail. Students will also learn the basic concepts of supramolecular chemistry, with references to environmentally and economically sustainable organic reactions.

In accordance with the Dublin Descriptors, the course learning outcomes are:

D1 - Knowledge and understanding - Students must demonstrate mastery of the fundamental concepts of organic chemistry. They must be able to rationalize structure-property relationships. In particular, they must understand synthetic methods for macrocyclic systems as well as the purification and characterization of these organic compounds, while analyzing their applications in molecular recognition.

D2 - Applying knowledge and understanding - Students must be able to apply the knowledge they have acquired in an appropriate and flexible manner to devise synthetic routes for relatively complex organic molecules. Furthermore, they must demonstrate the ability to use methodologies for the purification and characterization of chemical compounds.

D3 - Making judgments - Students must demonstrate critical reasoning skills and the ability to work in a group. They must be able to evaluate which analysis or characterization techniques are best suited to identifying the most appropriate solutions for the synthesis of organic molecules. Additionally, students must be able to assess which analysis or characterization techniques are most suitable for solving problems associated with these processes. D4 - Communication skills - Students must be able to communicate the concepts acquired during the course clearly and using appropriate, rigorous chemical terminology—both in writing and orally—enabling them to engage in informed discussion based on their own independently developed judgment.

D5 - Learning skills - Students must demonstrate that they have developed the ability to learn and delve deeper into course topics, thereby equipping themselves to handle future academic or professional paths with ease and to solve interdisciplinary problems.

Information for students with disabilities and/or specific learning disorders (SLD)

To ensure equal opportunities and in compliance with current legislation, interested students may request a personal meeting to plan any necessary compensatory measures and/or dispensations, tailored to the educational objectives and their specific needs.

The teaching will take place through the discussion of the various topics reported in the program and will include days dedicated to the clarification of doubts and the simulation of the oral exam. A laboratory credit is included, during which students will carry out the synthesis of macrocyclic systems aimed at studying their recognition properties in solution.Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus. Learning assessment may also be carried out on line, should the conditions require it.

Knowledge of the topics developed in the Organic Chemistry courses of the Bachelor's Degrees in Chemistry or Industrial Chemistry

Attendance at a minimum of 70% of the lessons is mandatory, in accordance with Article 27 of the University’s Teaching Regulations.

SYNTHETIC STRATEGIES FOR MACROCYCLIC BUILDING BLOCKS

Corona ethers, lariat corona ethers, cyclophanes, cryptands, metacyclophanes in 1,3-alternate conformation, calixarenes, heterocalixarenes, resorcarenes, hexameric capsules, immobilization via intrabridging, cavitands, carcerands and hemicarcerands), cyclodextrins, pseudorotaxanes. 'One-pot' synthesis and 'convergent' synthesis of calixarenes.

ASYMMETRIC SYNTHESIS

Introduction and principles - Addition to carbonyl compounds - a-substitution with chiral enolates - Asymmetric aldolic reactions - Addition to double bonds C-C - Reduction and oxidation - Transpositions - Hydrolysis and esterification

LABORATORY ACTIVITIES

Synthesis of macrocyclic derivatives and their applications in host-guest chemistry and molecular recognition.

1) Notes from lessons

2) P. Y. BRUICE - Chimica organica - 3a Edizione EdiSES

3) W.H. BROWN e altri autori - Chimica Organica 5a Edizione EdiSES

4) STUART WARREN “Designing Organic Syntheses”, John Wiley &Sons

5) GARRY PROCTER “Sintesi Asimmetrica”, Edizione EdiSES

6) PAUL ANASTAS and JOHN WARN “Green chemistry theory and practice - Oxford University Press Inc.

The final exam consists of an oral test. A report is required for the laboratory activities that will be subject to assessment.The oral exam consists in the discussion of the topics covered in the course and is aimed at verifying the knowledge and skills acquired by the student, his ability to connect the various topics covered with current problems and his ability to use an appropriate language in the expose the proposed topics. Verification of learning can also be carried out electronically, should the conditions require it.

Laboratory activities. Synthesis of macrocyclic compounds (crown ethers, cryptands, calixarenes, resorcinarenes, cavitands). Asymmetric synthesis: synthesis of chiral auxiliaries, addition reactions to carbonyl compounds, asymmetric aldol condensation.