Advanced Methods in Organic Synthesis

Course goals
The objective of the course is to make students develop a fundamental base of knowledge of the most innovative organic reactions in the realm of organic synthesis.

Acquired skills
At the end of the course, the student should be able to select suitable reactions for a particular organic synthesis, based on the identification of the most effective possibilities among the available ones.

Course content
- Reactions involving transition metals. Preparation and structure of organocopper reagents, reactions involving organocopper reagents and intermediates. Reactions involving organopalladium intermediates: palladium-catalyzed nucleophilic substitution and alkylation, the Heck reaction, palladium-catalyzed cross-coupling reactions, carbonylation reactions. Reactions involving other transition metals (organonickel compounds, reactions involving rhodium and cobalt). [2.0 credit]
- The olefin metathesis reaction: RCM (Ring Closing Metathesis), ROM (Ring Opening Metathesis), CM (Cross Metathesis), RCAM (Ring Closing Alkyne Metathesis), Enyne RCM, Enyne CM. Catalysts and reaction mechanism. Synthetic applications. [1.5 credit]
- Carbon-carbon bond-forming reactions of compounds of boron, silicon and tin. Organoboron compounds: synthesis of organoboranes; carbonylation and other one-carbon homologation reactions; homologation via alpha-halo enolates;stereoselective alkene synthesis; nucleophilic addition of allylic groups from boron compounds. Organosilicon compounds: synthesis of organosilanes; general features of Carbon-Carbon bond-forming reactions of organosilicon compounds; addition reactions to aldehydes and ketones; reactions with iminium ions; acylation reactions; conjugate addition reactions. Organotin compounds: synthesis of organostannanes; Carbon-Carbon bond-forming reactions of organotin compounds. [2.0 credit]
- Total syntheses: examples using the above described methods. [0.5 credit]

Suggested prerequisites
Good knowledge of organic synthesis; ideally the course should be followed after attending Chimica Organica B (2° semester of the previous year).

Reference material
- F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science.

Assessment method
Written tests (2 tests "in itinere") and final oral examination. Each written test is typically comprised of 10-15 exercises taken from the recommended book (Carey & Sundberg, Part B). The final oral exam is mainly focused on a discussion of the written tests.

Language of instruction
English

Attendance policy
Strongly recommended

Mode of teaching
Traditional

Other information
Level of course: advanced