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Stereoselective organic syntheses - AP110012

Title:	Stereoselective organic syntheses
Guaranteed by:	Department of Organic Chemistry (110)
Faculty:	Faculty of Chemical Technology
Actual:	from 2019
Semester:	winter
Points:	winter s.:0
E-Credits:	winter s.:0
Examination process:	winter s.:
Hours per week, examination:	winter s.:3/0, other [HT]
Capacity:	unknown / unknown (unknown)
Min. number of students:	unlimited
State of the course:	taught
Language:	English
Teaching methods:	full-time
Teaching methods:	full-time
Level:
Note:	course is intended for doctoral students only can be fulfilled in the future

Guarantor:	Hodačová Jana doc. Dr. Ing.
Classification:	Chemistry > Organic Chemistry
Interchangeability :	P110012

Examination dates

Annotation -

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)

Aim of the course -

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)

Course completion requirements -

To pass two semestral tests and a final exam.

Last update: Pátková Vlasta (19.11.2018)

Literature -

Recommended:

Stereochemistry of organic compounds, Eliel, Ernest Ludwig, Wilen, Samuel H., Mander, Lewis N., 1994

Organic chemistry, Clayden, Jonathan, Greeves, Nick, Warren, Stuart G., 2012

Principles of asymmetric synthesis, Gawley, Robert E., Aubé, Jeffrey, 2012

Optional:

Stereoselective Synthesis in series Methods of Organic Chemistry (Houben-Weyl), Vols. E21a-E21f,, Helmchen, Günter, Hoffmann, Reinhard W., Mulzer, Johann, Schaumann, Ernst, 1995

Last update: Hodačová Jana (16.08.2024)

Teaching methods -

Lectures and seminars

Last update: Pátková Vlasta (19.11.2018)

Syllabus -

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)

Learning resources -

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)

Entry requirements -

Knowledge of organic chemistry and organic synthesis at the Master level.

Last update: Pátková Vlasta (19.11.2018)