General objectives: Knowledge of the basic concepts of stereochemistry and stereoselective sinthesis.
D1. Knowledge and understanding: Students at the end of the course must know the stereochemical nomenclature, the concept of stereogenicity, of relative and absolute stereoselectivity.
D2. Applying knowledge and understanding: Students at the end of the course will apply the aquired knowledge to recognize the stereogenic and prostereogenic elements of a molecule, the spatial relationships among groups, and to analyze the stereochemical outcome of a reaction starting from prochiral molecules.
D3. Making judgements: Students at the end of the course will be able to select in autonomy the most efficient methods of control of the relative and absolute stereochemistry of a simple asymmetric transformation.
D4. Communication skills: students are expected to present with appriopriate language the aquired concepts, using the correct stereochemical notations.
D5. Learning abilities: Students are expected to learn from lessons, from the book, and to elaborate in autonomy the concepts given in the course aimed at the acquisition of the modern concepts of asymmetric synthesis.

General Organic chemistry. Fundamentals of stereochemistry (Stereoisomers, absolute and relative stereochemistry, stereochemical descriptors, conformational analysis).

Stereochemical analysis. Chirality related to the presence of stereogenic axex and planes. Methods of resolution of racemic mixtures. Control of relative and absolute stereochemistry.Asymmetric induction by auxiliaries, reagents and chiral catalysts. Chiral pool strategy.

Defininitions: stereoisomerism, diastereoisomerism, enantiomerism. Configurations. Stereochemical notations. D,L and R,S. Conformations. Klyne nomenclature.
Symmetry, elements and operations. Chiral point groups. Stereogenic units. Central, axial, planar, inherent chirality. Descriptors.
3. Polarimetry and circular dichroism.. 4.Topicity. Homotopic, diastereotopic and enantiotopic groups and faces. Prochiral molecules. Re, Si, pro-R, pro-S descriptors. Correct tridimentional writing.
5. Resolution of racemates.Classical, kinetic, dinamic resolution. Physical resolution. Chiral stationary phases. E.e. determination via chiral HPLC, GC , NMR (Mosher derivatives, Shift reagents). Racemiztion. Use in dynamic kinetic resolutions.
6. Selectivity. Substrate and product selectivity. Diastereo- and enantioselectivity. Kinetic background.
7.Diastereoselectivity: A) Nucleophilic additions to C=O . Additions to cycloalkanones. Addition to C=O of linear carbonyl compounds with an alpha stereogenic centre. Felkin Ahn, model, even with alpha-electronegativ groups. Chelate model. B) Aldol reactions: generality. Lithium and Boron enolates.
8. Asymmetric synthesis. A) Substrate-based asymmetric induction. Chiral auxiliary strategy in: alfa-alkylation of carboxylic acids and carbonyl compounds, nucleophilic addions to C=O, aldol reactions. B) Asymmetric induction based on chiral reagents in asymmetric reductions of prochiral ketones, hydroboratio/oxidation. C) Asymmetric induction based on chiral catalysts in: asymmetric reductions of prochiral ketones, epoxidations, aldol reactions. Organocatalysis, generality and examples.
9. Chiral pool strategy. Aminoacids transformations. Synthesis of ipsenol and sulcatol.

32 hours lectures in class, supported by power point slides which are furnished to the students on Moodle platform, and examples on the blackboard.

The level of knowledge and understanding achieved by the student is ascertained by an oral examination, covering all the topics of the program. Three to five open questions are asked, both theoretical and practical. The evaluation is given out of thirty, and takes into account the knowledge and understanding, but also the exposure, the correctness of the language and the ability to link the topics.

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