Ateneo - UPO

The course begins by paying particular attention to stereoselective syntheses and to the use of chiral pool, chiral auxiliaries other than chiral catalysts (organic or metal complexes) for asymmetric synthesis.
Then, various types of pericyclic and cycloaddition reactions, including click reactions will be examined. Aromatic and saturated heterocyclic chemistry, radicalic and rearrangement reactions will be also considered. Finally, non-conventional synthetic approaches such as sonochemistry, mechanochemistry, microwave and flow chemistry will be analyzed.
For each of these subjects we will show practical application examples in the various fields of chemistry and particularly to green chemistry approaches.

J. Clayden, N. Greeves, S. Warren, Organic Chemistry , 2nd Edition, Oxford University Press 2012 (ISBN 978-0-19-927029-3).
F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reaction and Synthesis, Springer (ISBN 978-0-387-71481-3).
Slides and other material given by the teacher.

The course is designed to increase the organic chemistry knowledge acquired during the Batchelor degree by studying important class of organic reactions and synthetic strategies not explained on other organic chemistry courses. The students will obtain the principles of modern synthetic strategies: pericyclic reactions, asymmetric synthesis, heterocyclic chemistry using also non-conventional and greener approaches.
Special attention will be given to the ability of understanding, designing and drawing reaction mechanisms by selecting the best pathway of organic reactions, also stereoselective or sterospecific and with green chemistry approaches.
Communication skills: the students will be able to use a suitable chemical vocabulary in relation to advanced organic chemistry Learning skills and ability in making judgements about new organic reactions.

Contents of the Organic Chemistry courses of the Batchelor Degree.

The course is based on classroom lectures and exercises. During the lessons, the literature references for various topics will be given to enable further investigation and encourage the student to read the primary literature.
The concepts of the course will be discussed in the classroom and applied directly during exercises in the classroom.

The teacher is available to the student for any clarification or explanation of the topics covered during the course.
Ongoing learning will be assessed through classroom exercises and collegial discussions.
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/servicesstudents-physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

The exam consists of a presentation of a research carried out by the student on a particular chosen subject specifying also the experimental part, followed by an oral examination consisting of 2-3 questions on the entire program of the course. The evaluation will take place based on the efficacy of the presentation and by testing the level of the learning objectives previously described. The passing grade is achieved by demonstrating that the student has understood the subject and is able to use the basic concepts of the topics covered during the course through the exercises. The ability to correctly write formulas and reaction mechanisms in the written exam and on the blackboard is also essential in order to pass the exam.
Other parameters of judgment are: the ability to organize and clearly expose the answer and the acquisition of the appropriate terminology. Excellence can be achieved by demonstrating a strong ability to link-compare different topics covered during the course.

Pro-chiral centres and stereoselectivity in additions to alkenes and carbonyls: Felkin-Ahn model and chelate effect. Chiral pool and chiral auxiliary; enantiomeric excess. Asymmetric catalysis in hydrogenation, epoxidation and dihydroxylation reactions. CBS reagent and BINAP. Asymmetric synthesis of C-C bonds. Asymmetric aldolic reactions. Enzymes as catalysts. Stereoselectivity in cyclic molecules.
Pericyclic reactions: 1,3-dipolar cycloadditions; click chemistry; sigmatropic rearrangements, electrocyclic reactions.
Heterocyclic compounds and their derivatives (main heterocyclic compounds with one and with two heteroatoms, pyrrole, furan, thiophene, diazoles, pyridine, diazines, triazines, indole). Functionalization of pyridines; synthesis of aza-heterocycles via cycloaddition and sigmatropic rearrangements; synthesis and chemistry of azoles and other heterocycles with two or more heteroatoms.
Rearrangement reactions: vicinal group participation; Payne, pinacol, and Favorskii rearrangement: migration to heteroatoms: Baeyer-Villiger and Beckmann rearrangement; fragmentations and ring expansions; migrations to carbenes and nitrenes. Radicalic reactions: analysis of examples and applications.
Non-conventional synthetic approaches such as sonochemistry, mechanochemistry, microwave and flow chemistry. Examples of synthetic and industrial applications.

Objective 1: Knowledge and understanding.
Knowledge of the principles of stereoselective and stereospecific synthesis.
Knowledge of the frontier orbital theory and its use to explain reactivity, stereospecificity and regioselectivity of periciclic reactions.
Knowledge of the properties of heterocyclic systems.
Objective 2: Applying knowledge and understanding.
Ability to design a stereoselective and stereospecific synthesis.
Ability to explain specific reaction mechanisms.
Ability to apply the frontier orbital theory to explain reactivity, stereospecificity and regioselectivity of periciclic reactions.
Ability to compare the properties of heterocyclic systems and to propose synthesis and functionalization strategies.
Ability to carry out bibliographic and structural searches on organic molecules and reactions.
Ability to find a stereoselective synthesis for a chiral molecule.
Ability to explain the course and the stereochemistry of a reaction based on its mechanism.
Ability to discuss the possible reaction pathway according to the structure of the reagents and the reaction conditions.
Objective 3: Making judgements.
Ability to evaluate from the structure of a compound which predictions can be made about its molecular properties.
Ability to interpret and rationalize organic reactions in terms of reaction mechanism and to address the study of the subject through critical and non-mnemonic learning.
Objective 4: Communication skills.
Ability to prepare and give a presentation clear and functional on an advanced scientific paper or subject.
Ability to connect and compare different topics.
Ability to clearly organize and explain the answer by acquiring the appropriate terminology.
Objective 5: Learning skills
Ability to use teaching material for a critical and rational study.
Ability to update and expand knowledge of the discipline through the consultation of more advanced teaching texts and scientific publications on the subject.