Learning objectives
In recent past years, the discovery of novel and ever-sophisticated synthetic methods and techniques to access function-rich natural and non-natural organic molecules is an open field of inquiry, with wide impact on allied disciplines as bio-organic chemistry, medicinal chemistry, chemical biology, pharmacology, pharmaceutical technology.
On these premises, one main goal of this course is devoted to widening the basic knowledge on organic synthesis, by approaching chemical reactions and organic synthesis methods which were not mentioned in previous organic chemistry courses. The central themes of the course are intended to provide the student with a knowledge in the organic synthesis field which may be useful in the context of future professional engagement in the pharmaceutical and chemistry industry.
Prerequisites
To fully appreciate the content of the course, it is necessary to acquire knowledge of organic chemistry basics in previous courses. To access the final examination, it is necessary to pass the Organic Chemistry Basics/Organic Chemistry” exam (Pharmacy) or Organic Chemistry I (CTF), or similar organic chemistry courses.
Course unit content
The following topics will be treated:
.Recall of basic carbon-carbon bond-forming reactions as gained by previous organic chemistry courses
.Recall of the frontier molecular orbital theory
.Thermal cycloaddition reactions (Diels-Alder reaction, 1,3-dipolar cycloadditions)
.Photochemical cycloaddition reactions
.Sigmatropic rearrangements
.Electrocyclic reactions
.Transition metal-catalyzed carbon-carbon bond-forming reactions
.Olefin metathesis
.Organocatalysis
Full programme
The following topics will be treated:
Recall of basic carbon-carbon bond-forming reactions as acquired by previous organic chemistry courses
Recall of the frontier molecular orbital theory
Thermal cycloaddition reactions (Diels-Alder reaction, inverse electron demand Diels Alder reaction, hetero-Diles Alder, Alder-ene, 1,3-dipolar cycloadditions with nitrones, azamethyne ylides, azides)
Photochemical cycloaddition reactions
Sigmatropic rearrangements (Claisen, Ireland-Claisen, Johnson, Cope, .)
Electrocyclic reactions
Transition metal-catalyzed carbon-carbon bond-forming reactions (principles, Heck, Suzuki-Miyaura, Sonogashira and other cross-couplings)
Olefin methatesis
Organocatalysis (principles, activation modalities, application in asymmetric synthesis, multicatalysis)
Bibliography
J. Clayden, N. Greeves, S. Warren, Organic Chemistry, Second Edition, 2012, Oxford University Press.
Teaching methods
According to the above mentioned objectives and contents, the course is carried out through frontal oral lessons (theory and exercises).
Assessment methods and criteria
The final examination consists of a written exam dealing with the execution of exercises on the synthesis and reactivity of organic compounds. This test is aimed at verifying whether the student has developed the skill and ability of selecting and deploying information from the theory study in order to furnish solutions to a given practical organic chemistry problem. The result of the written exam is marked as optimum, good, adequate, inadequate. A minimum of adequate is required as a threshold.
Other information
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