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Lecturer(s)
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Course content
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Winter term Lecture No. 1 Introduction to the organometallic chemistry - retrosynthesis. Organometallic compounds of magnesium. Lecture No.2 and No.3 Group 4: Titanium and Zirconium Lecture No.4 and No.5 Group 11 and 12: Copper and Zinc Lecture No.6 and No.7 Group 13: Aluminum, Gallium, and Indium Lecture No.8 and No.9 Chrome, tin, and silicon. Lecture No.10 and No.11 Complexes of silver and gold. Lecture No.12 and No.13 Applications of organometallics in natural product synthesis showcase examples Summer Term Lecture No.1 and No.2 Introduction to the transition metal-catalyzed organic transformations. Introduction to the reaction mechanisms of transition metal-mediated reactions. Lecture No.3 and No.4 The role of ligands on the relevant catalytic steps. Lecture No.5 and No.6 Palladium and Nickel-catalyzed reactions and natural product synthesis. Lecture No.7 and No.8 Ruthenium mediated metathesis reactions and natural product synthesis. Lecture No.9 and No.10 Asymmetric catalytic hydrogenation and natural product synthesis. Lecture No.11 till 13 Asymmetric hydroformylation and iridium promoted C-C bond forming reactions in natural product synthesis.
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Learning activities and teaching methods
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Lecture, Dialogic Lecture (Discussion, Dialog, Brainstorming)
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Learning outcomes
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The goal of the lecture is to present an overview of the chemical properties and synthetic applications of organometallic compounds and complexes. A special place in the lecture is given to metals, and complexes of the metals; contained within the group 2, 4-6, and 11-13. The influence of the metal oxidation state, radius, and valence to the properties of a newly generated organometallic compound, in the context of chemo- and stereoselectivity of chemical transformations will be discussed. The second term is focused on the introduction into the world of transition metal catalysis. The impact of transition metal catalyzed reactions on the organic synthesis, and especially natural product synthesis will be discussed. The power of such transformations will be demonstrated on selected total syntheses of several complex natural products. The impact of organometallic reagents in the field of modern organic synthesis is demonstrated on selected total syntheses of various complex natural products. In some cases, the structure of natural products virtually dictated the development of new synthetic methods and led us, organic chemists, to the development of new organometallic reagents possessing new chemo and/or stereoselectivity. The main goal of the lecture is to allow students to use organometallic reagents as standard synthetic tools when planning their synthesis. Thus, the lecture will not only give the overview of the latest organometallic reagents and transformations but will also focus on the retrosynthetic planning of complex natural products prepared with use of organometallic compounds.
Gained abilities - Gained overview over the use of standard organometallic reagents - Be able to decide which reagent should be used in context of given target - Synthetic planning retrosynthesis of complex natural products with help of organometallic compounds
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Prerequisites
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Interview in English language (general topic - should only reveal the communication skills in English). Student must have knowledge acquired within all basic lectures of organic, inorganic and physical chemistry. Lecture enrollment is conditional upon successful completion of an entry test. The test will be carried out by the lecturer.
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Assessment methods and criteria
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Written exam, Seminar Work
A student must have knowledge acquired within all basic lectures of organic, inorganic and physical chemistry. Lecture enrollment is conditional upon successful completion of an entry test. The test will be carried out by the lecturer. Exam (written): given on the basis of written seminal work that will focus in detail on transition metal catalyzed step(s) of the synthesis of the discussed natural product (molecule taken from recent literature) topic selected by the lecturer. It is expected that the presented work will include a detailed discussion about the used transition metal-mediated. Written work must be max 5 pages long (Times new roman 11 pts A4 1.1 interlined) including the pictures, figures, and schemes. Based on the written part, oral discussion of the exam (whiteboard) will follow.
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Recommended literature
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Crabtree, R. H. (2009). The organometallic chemistry of the transition metals. Hoboken, N.Y: Wiley.
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Robert B. Jordan. (2007). Reaction mechanisms of inorganic and organometallic systems. Oxford: Oxford University Press.
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Schlosser, M. (2002). Organometallics in synthesis: a manual. Chichester: John Wiley & Sons VCH.
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