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The course Stereoselective Organic Syntheses includes basic organic stereochemistry, physico-chemical aspects of stereochemical transformations, analytical methods applicable to the studies of stereoizomers and stereoselective reactions, and methods of stereoselective syntheses of organic compounds. A series of diastereoselective and enantioselective organic reactions will be presented, and advantages or disadvantages of particular synthetic approaches will be discussed.
Last update: Pátková Vlasta (19.11.2018)
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To pass two semestral tests and a final exam. Last update: Pátková Vlasta (19.11.2018)
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R: Eliel, E. L.; Wilen, S. H.: Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994. ISBN 978-0-471-01670-0.
R: Gawley, R. E.; Aubé, J.: Principles of Asymmetric Synthesis, 2nd edition, Elsevier, Oxford, 2012. ISBN 978-0-08-044860-2 (e-book 978-0-08-0914138).
A: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.: Stereoselective Synthesis v serii Methods of Organic Chemistry, Houben-Weyl, Vol. 21a-21f, 4. vydání, Thieme, Stuttgart, 1995. ISBN 9783131001146. Last update: Hodačová Jana (16.08.2024)
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Lectures and seminars Last update: Pátková Vlasta (19.11.2018)
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1. Introduction to stereochemistry of organic compounds.
2. Stereochemical nomenclature.
3. Racemization, enantiomerzsation, diastereomerization.
4. Analytical methods in organic stereochemistry.
5. Enantiomerically pure natural compounds.
6. Racemates resolutions.
7. Overview and principles of stereoselective reactions.
8. Diastereoselective reactions.
9. Enantioselective reactions using a stoichiometric amount of a chiral reagent.
10. Enantioselective catalysis with the metal complexes.
11. Enantioselective organocatalysis.
12. Enantioselective catalysis with enzymes.
13. Comparison of the methods of stereoselective syntheses. Last update: Pátková Vlasta (19.11.2018)
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A teacher will provide the study materials related to the lectures.
E-books available through the NTK web pages:
Mislow, K.: Introduction to Stereochemistry. Dover Publications, 2002. https://app.knovel.com/web/toc.v/cid:kpIS000015/viewerType:toc//root_slug:viewerType%3Atoc/url_slug:root_slug%3Aintroduction-stereochemistry?kpromoter=federation
Wolf, C.: Dynamic Stereochemistry of Chiral Compounds - Principles and Applications. Royal Society of Chemistry, 2007. https://app.knovel.com/web/toc.v/cid:kpDSCCPA01/viewerType:toc//root_slug:viewerType%3Atoc/url_slug:root_slug%3Adynamic-stereochemistry?kpromoter=federation
Jozwiak, K.: Drug Stereochemistry. 3rd edition. CRC Press, Boca Raton, 2012. https://www.taylorfrancis.com/books/e/978142009239
Torres, R. R.: Stereoselective Organocatalysis. JohnWiley & Sons, Inc., Hoboken, New Jersey, 2013. https://onlinelibrary.wiley.com/doi/book/10.1002/9781118604755
Schreier, P.; Huffer, M.; Bernreuther, A.: Analysis of Chiral Organic Molecules: Methodology and Applications. De Gruyter, Berlin, 1995. http://web.a.ebscohost.com.ezproxy.techlib.cz/ehost/detail/detail?vid=0&sid=9a38914a-8de0-44ec-a42d-0678d7e8cfe5%40sessionmgr4010&bdata=Jmxhbmc9Y3Mmc2l0ZT1laG9zdC1saXZl#AN=559497&db=nlebk Last update: Pátková Vlasta (19.11.2018)
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Students will be able to:
do stereochemical analysis of organic compounds and their reactions
propose a suitable synthetic method for preparation of the desired stereoizomer of a product
select a suitable analytical method for studies of stereoizomers and stereoselective reactions Last update: Pátková Vlasta (19.11.2018)
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Knowledge of organic chemistry and organic synthesis at the Master level. Last update: Pátková Vlasta (19.11.2018)
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