Protecting groups. Concept of orthogonality in protecting groups. Protection of alcohols and 1,2- and 1,3-diols; protection of carbonyl compounds; amine protection; thiol protection.
Transformation of functional groups. Oxidation and reduction reactions: overview, effect of heteroatoms on the oxidation state of carbon; common oxidation reactions and oxidizing agents. Oxidation of alcohols, diols, aldehydes, ketones, alkenes, alkynes, allyl carbons and benzyls, oxidation of ketones α-carbons. Common reduction reactions and reducing agents; catalytic hydrogenation; hydrides and metals as reducing agents.
Carbon-carbon bond formation using organometallic reagents. Grignard reagents, organolithium, organotitanium, organocerium, organocopper, organozinc, organoboron, organosilicon and organogold reagents.
Palladium-catalyzed carbon-carbon bond formation reactions: compatibility with functional groups, leaving group reactivity, selectivity, steric and electronic effects. Organolithium and organomagnesium reagents (Kumada reaction); organozinc reagents (Negishi reaction); organometallic reagents based on aluminum and zirconium; organotin reagents (Stille reaction); organoboron reagents (Suzuki reaction); organosilicon reagents (Hiyama reaction). Homocoupling reactions; coupling of enolates and phenoxides. Reaction of Buchwald-Hartwig and Ullmann coupling. Activation of the C-H bond. Reaction of Fujiwara-Moritani. Coupling of biaryl derivatives. Carbonyl coupling reactions: synthesis of ketones and carboxylic acid derivatives; carbonylation of alkenes and alkynes. The Heck reaction: reaction of insertion of alkenes and alkynes on arenas catalysed by palladium.
Unsaturated carbon-carbon bond formation. Formation of double bonds: reactions of phosphorus ilides (Wittig reaction) and sulfur. Peterson elimination. Allyl silanes as nucleophiles. Formation of triple carbon-carbon bonds.
Introduction to multi-step reactions applied to the synthesis of compounds of pharmacological interest.
Lecture notes by the Professor, examples of exercises and cases of study proposed during the examination. All this material is available at the website on Elly platform from the beginning of the course. It constitutes the main support for the preparation of the exam.
• George S. Zweifel, Michael H. Nantz, Peter Somfai – Modern Organic Synthesis, An Introduction 2nd Ed., Wiley, 2017, ISBN: 9781119086536
• Michael Smith – Organic Synthesis, 4th Ed., Academic Press, 2016, ISBN: 9780128007204
The format of the class will be lectures of two hours each spread over two days per week A regular class meetings will be composed of lecture and class exercises.
The lectures will be held in blended mode, i.e. in the classroom and in streaming through the digital platform Microsoft Teams. These lessons will also be recorded and made available to students on the digital platform Microsoft Stream. The connection to this digital platform will be guaranteed through a web link that students will find on the course website on the Elly digital platform.